Great Oak Manor Reviews

Reviews

Awards

23

+26 User photos

• Featured

  Emily R. Sent on 02/14/2022
  5 out of 5 rating

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  Magical Venue

  Great Oak Manor was the kind of venue we had always dreamed about. It was like the stars aligned for us to have our wedding here. My husband found the venue when we had to go to Chestertown for work (does a groom ever find **THE** venue??), we saw it in May 2020, and knew it was the venue but we were still unsure of booking because of the pandemic. When we toured we met Holly (who adds part of the magic to Great Oak Manor!) She was so lovely to talk to and she was understanding that we weren’t able to book due to the uncertainty. In January 2021, we decided we weren’t going to wait any longer to get married and started our planning again and GOM was booked over all of the weekends in 2021, so then we were considering a week day wedding there.. but like magic.. a full weekend opened up! We were able to have our dream venue in June 2021! We booked out the entire manor for the weekend and had a small 50 person wedding! Half of our guests stayed at the manor and the other half stayed around the corner at the Great Oak Lodge or in AirBnBs around Chestertown. We loved staying in the carriage house (I took a bath every day!!). The weekend was so magical. We had a welcome reception on Friday in the conservatory (while it rained). And we had an outdoor ceremony and an open air reception the next day (like magic it was a sunny day and the ground was luckily not wet from all the rain the day before). We had the most beautiful sunset on our wedding day— absolutely breathtaking! It is such a beautiful venue with so many great places for photo ops, from the front of the manor, to the beautiful staircase, to the library, to the beach. Our guests absolutely loved it and enjoyed the other amenities offered like kayaking and the fun golf carts and 9-hole golf course nearby. The breakfast was delicious (GOM also hosted and prepared a delicious breakfast spread for all of our guests on Sunday to close out our weekend). We also loved that it was dog friendly and we were able to bring our dog with us, he really enjoyed his stay too! Holly and Joe and the rest of the staff showed us such exceptional hospitality, we are so grateful for them! Holly recommended some amazing vendors to work with as well. They helped us to bring our vision to life and Great Oak Manor will always be a special place for us to return to year after year.

  Great Oak Manor was the kind of venue we had always dreamed about. It was like the stars aligned for us to have our wedding here. My husband found the venue when we had to go to Chestertown for work (does a groom ever find **THE** venue??), we saw it in May 2020, and knew it was the venue but we were still unsure of booking because of the pandemic. When we toured we met Holly (who adds part of the magic to Great Oak Manor!) She was so lovely to talk to and she was understanding that we weren’t able to book due to the uncertainty. In January 2021, we decided we weren’t going to wait any longer to get married and started our planning again and GOM was booked over all of the weekends in 2021, so then we were considering a week day wedding there.. but like magic.. a full weekend opened up! We were able to have our dream venue in June 2021! We booked out the entire manor for the weekend and had a small 50 person wedding! Half of our guests stayed at the manor and the other half stayed around the corner at the Great Oak Lodge or in AirBnBs around Chestertown. We loved staying in the carriage house (I took a bath every day!!). The weekend was so magical. We had a welcome reception on Friday in the conservatory (while it rained). And we had an outdoor ceremony and an open air reception the next day (like magic it was a sunny day and the ground was luckily not wet from all the rain the day before). We had the most beautiful sunset on our wedding day— absolutely breathtaking! It is such a beautiful venue with so many great places for photo ops, from the front of the manor, to the beautiful staircase, to the library, to the beach. Our guests absolutely loved it and enjoyed the other amenities offered like kayaking and the fun golf carts and 9-hole golf course nearby. The breakfast was delicious (GOM also hosted and prepared a delicious breakfast spread for all of our guests on Sunday to close out our weekend). We also loved that it was dog friendly and we were able to bring our dog with us, he really enjoyed his stay too! Holly and Joe and the rest of the staff showed us such exceptional hospitality, we are so grateful for them! Holly recommended some amazing vendors to work with as well. They helped us to bring our vision to life and Great Oak Manor will always be a special place for us to return to year after year.

  • +7 photos

  Great Oak Manor's reply:

  Emily, your write so beautifully. Thank you for taking the time to write such a detailed description of your experience with us. I loved working with you and it was a beautiful day with beautiful people. I wish you both the best that life has to offer you. Hugs!
• Sophie Sent on 05/12/2021
  5 out of 5 rating

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  Ideal venue, LGBTQ-friendly

  This place is the absolute best!! My wife and I got married in an elopement weekend during the COVID-19 pandemic in October 2020. The Great Oak Manor staff (especially Holly and Joe) went above and beyond in every way to make it a dream weekend, from working with our friends and family to deliver flowers and cheese platters to our room before arrival, to helping us coordinate with the photographer (Laura’s Focus Photography – incredible!) and officiant (Cheryl of Celebrations-by-Cheryl -- also incredible!) before and on the big day, to even arranging for a kayaking session in our wedding dresses, which made for some amazing wedding photos! Our suite was lovely (Marmaduke), the grounds were exquisite, and the breakfasts and wedding night dinner were delicious. We can’t overstate how much we recommend this venue for an elopement weekend, for LGBTQ+ couples or any couples!

  This place is the absolute best!! My wife and I got married in an elopement weekend during the COVID-19 pandemic in October 2020. The Great Oak Manor staff (especially Holly and Joe) went above and beyond in every way to make it a dream weekend, from working with our friends and family to deliver flowers and cheese platters to our room before arrival, to helping us coordinate with the photographer (Laura’s Focus Photography – incredible!) and officiant (Cheryl of Celebrations-by-Cheryl -- also incredible!) before and on the big day, to even arranging for a kayaking session in our wedding dresses, which made for some amazing wedding photos! Our suite was lovely (Marmaduke), the grounds were exquisite, and the breakfasts and wedding night dinner were delicious. We can’t overstate how much we recommend this venue for an elopement weekend, for LGBTQ+ couples or any couples!

  Great Oak Manor's reply:

  Thank you so much for your great review of your elopement experience at the Manor last Fall. We appreciate your choosing Great Oak Manor for your special day and we enjoyed being a part of it. Your recommendation for us as a wedding venue is so appreciated and it will definitely help others as they travel the same path you did. Stay well and happy.
• Katherine Sent on 10/09/2020
  5 out of 5 rating

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  Where pure luxury and warm hospitality meet on the Chesapeake Bay!

  My new husband and I first fell in love with this picturesque, hidden gem when we toured as a potential wedding venue in Oct. 2019. We were not only memorized by the beauty of the property and the sense of calmness and serenity we felt while visiting, but we were so at ease and impressed with the hospitality when speaking with the main Inn Keeper, Holly about the possibility of hosting our 2020 nuptials there. We had been to several nice waterfront properties up and down the Eastern Shore before we went to Great Oak, but none held a candle to GOM and all it had to offer. Driving into the gates and up the gravel drive, we knew we'd eventually marry at the the Manor, and so we signed a contract that day and never looked back. Fast forward 1 year and few wedding bands later, we know without a shadow of a doubt that Great Oak was the perfect home away from home to host our closest friends and family for what has now become the best day of our lives to date. Every time we have stayed at the Manor, both before and after the wedding, the staff has rolled out the red carpet and made us feel so special. And I personally have no words for how enchanting our actual wedding day was from start to finish, how exceptional the whole wedding weekend was - from welcome bonfires to waterfront yoga to relax - words alone are not adequate. We've been told by guests that our event felt like "a summertime lawn party you only see in the movies." But more importantly, Holly, Joe, Lizzie and the rest of the GOM bunch now feel like family to us. Its only been a week since our wedding and I am sad its over/ready to get married there all over again! The good news is we know that Great Oak Manor will hold a special place in our hearts and for our new family for years to come. We can hardly wait to go back for anniversaries and special events, and maybe one day bring our own little ones to visit the Manor and meet the very special people there. We're so glad we discovered this special place- its only an hour away from our home, but feels like worlds away in the very best sense of the meaning. Many thanks to everyone at Great Oak Manor and until next time!

  My new husband and I first fell in love with this picturesque, hidden gem when we toured as a potential wedding venue in Oct. 2019. We were not only memorized by the beauty of the property and the sense of calmness and serenity we felt while visiting, but we were so at ease and impressed with the hospitality when speaking with the main Inn Keeper, Holly about the possibility of hosting our 2020 nuptials there. We had been to several nice waterfront properties up and down the Eastern Shore before we went to Great Oak, but none held a candle to GOM and all it had to offer. Driving into the gates and up the gravel drive, we knew we'd eventually marry at the the Manor, and so we signed a contract that day and never looked back. Fast forward 1 year and few wedding bands later, we know without a shadow of a doubt that Great Oak was the perfect home away from home to host our closest friends and family for what has now become the best day of our lives to date. Every time we have stayed at the Manor, both before and after the wedding, the staff has rolled out the red carpet and made us feel so special. And I personally have no words for how enchanting our actual wedding day was from start to finish, how exceptional the whole wedding weekend was - from welcome bonfires to waterfront yoga to relax - words alone are not adequate. We've been told by guests that our event felt like "a summertime lawn party you only see in the movies." But more importantly, Holly, Joe, Lizzie and the rest of the GOM bunch now feel like family to us. Its only been a week since our wedding and I am sad its over/ready to get married there all over again! The good news is we know that Great Oak Manor will hold a special place in our hearts and for our new family for years to come. We can hardly wait to go back for anniversaries and special events, and maybe one day bring our own little ones to visit the Manor and meet the very special people there. We're so glad we discovered this special place- its only an hour away from our home, but feels like worlds away in the very best sense of the meaning. Many thanks to everyone at Great Oak Manor and until next time!

  Great Oak Manor's reply:

  Thank you so very much for your kind words, Katy. I appreciate your taking the time to write such a lengthy review of your wedding experience. You were such a joy to work with that you made my job so much easier. We do look forward to having you, your family and your friends visit again in the future.
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• Stacey Sent on 09/23/2020
  5 out of 5 rating

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  Amazing- Holly is incredible!

  Holly and Joe are incredible. Planned for the better part of a year, through COVID and was given so much support and treated like family when the time came. Holly is awesome.

  Holly and Joe are incredible. Planned for the better part of a year, through COVID and was given so much support and treated like family when the time came. Holly is awesome.
• Brittany Sent on 11/14/2019
  5 out of 5 rating

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  A loving, kind, warm venue

  This is a prefect venue for any kind of wedding. The scenery is beautiful. It is a wonderful venue.

  This is a prefect venue for any kind of wedding. The scenery is beautiful. It is a wonderful venue.
• Jenn Sent on 11/10/2019
  5 out of 5 rating

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  Gorgeous Venue, Friendly Staff, Flexible Atmosphere

  Great Oak Manor can provide you a wedding experience as small or as big as you want it to be in a flexible, affordable atmosphere.
  
  We visited Great Oak Manor and immediately fell in love with the venue. A private getaway right next to the water with an incredible view - not to mention a small beach, firepits, kayaks, and hammocks. Quiet, peaceful, and overall a great place to just unplug from the daily worries. The inside of Great Oak Manor was as beautiful as the outside which aleviated the worry of rain ruining the day.
  
  The packages at Great Oak were very affordable and realistic compared to other venues that we searched. We ended up choosing the Small Wedding Package with up to 25 people and chose a catered reception dinner. Holly was a phenomenal chef and catered our wedding reception dinner. Her and her staff took care of the wedding cake or in our case a cheesecake. We were able to add on to the floral package so all of the bridesmaids and groomsmen had floral arrangements. Since our wedding was small, we were able to take advantage of the tables and chairs on site. If we wanted to bring our dog, we could have done that too.
  
  We were married in October - we wanted a laid back, more personal / private wedding with immediate family to just enjoy the night without the stress. Although Tropical Storm Nestor decided to rain on our wedding day, Holly and the staff at Great Oak Manor were super accommodating and flexible by having an indoor and outdoor option available based on the weather conditions. We had our ceremony and reception in the Conservatory where we were able to bring our decorations, alcohol, and desserts to add our own flair for our big day. We were even able to use the Conservatory for breakfast the following morning to keep all of the family together!
  
  We stayed at the Carriage House over the weekend to unpack, prep for the wedding, clean up, and also just enjoy a day to ourselves. It is a nice house separated from the rest of the Manor with it's own bathrooms, kitchen, living / dining areas, and two bedrooms. We used it to store extra food, drinks, our decorations, but also for people to relax and socialize while the guests from the previous night were checking out. The bride had hair and makeup done for herself and the bridesmaids there as well.
  
  Overall, everyone loved Great Oak Manor. We couldn't ask for it to be any more perfect and it is a place that we will return to for years to come.

  Great Oak Manor can provide you a wedding experience as small or as big as you want it to be in a flexible, affordable atmosphere.
  
  We visited Great Oak Manor and immediately fell in love with the venue. A private getaway right next to the water with an incredible view - not to mention a small beach, firepits, kayaks, and hammocks. Quiet, peaceful, and overall a great place to just unplug from the daily worries. The inside of Great Oak Manor was as beautiful as the outside which aleviated the worry of rain ruining the day.
  
  The packages at Great Oak were very affordable and realistic compared to other venues that we searched. We ended up choosing the Small Wedding Package with up to 25 people and chose a catered reception dinner. Holly was a phenomenal chef and catered our wedding reception dinner. Her and her staff took care of the wedding cake or in our case a cheesecake. We were able to add on to the floral package so all of the bridesmaids and groomsmen had floral arrangements. Since our wedding was small, we were able to take advantage of the tables and chairs on site. If we wanted to bring our dog, we could have done that too.
  
  We were married in October - we wanted a laid back, more personal / private wedding with immediate family to just enjoy the night without the stress. Although Tropical Storm Nestor decided to rain on our wedding day, Holly and the staff at Great Oak Manor were super accommodating and flexible by having an indoor and outdoor option available based on the weather conditions. We had our ceremony and reception in the Conservatory where we were able to bring our decorations, alcohol, and desserts to add our own flair for our big day. We were even able to use the Conservatory for breakfast the following morning to keep all of the family together!
  
  We stayed at the Carriage House over the weekend to unpack, prep for the wedding, clean up, and also just enjoy a day to ourselves. It is a nice house separated from the rest of the Manor with it's own bathrooms, kitchen, living / dining areas, and two bedrooms. We used it to store extra food, drinks, our decorations, but also for people to relax and socialize while the guests from the previous night were checking out. The bride had hair and makeup done for herself and the bridesmaids there as well.
  
  Overall, everyone loved Great Oak Manor. We couldn't ask for it to be any more perfect and it is a place that we will return to for years to come.

  Great Oak Manor's reply:

  Jenn, thank you so much for this detailed review. So helpful to others. I appreciate your kind words and your assessment of the food and service of Great Oak Manor. We look forward to seeing you and Mitch very soon.
• Paige R. Sent on 01/12/2019
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  Great Oak review

  Great oak has been a pleasure to work with and we are very much looking forward to a magical experience. We cannot recommend them highly enough

  Great oak has been a pleasure to work with and we are very much looking forward to a magical experience. We cannot recommend them highly enough

  Great Oak Manor's reply:

  Why thank you Paige. And we haven't even made it to the good part yet. It has been a pleasure working with you both as well.
• Paula E. Sent on 10/14/2021
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  Amazing wedding weekend !

  Great Oak Manor is the perfect wedding venue ! Everything in the Manor is beautifully appointed. The grounds are gorgeous , the rooms beautiful and the staff so very pleasant and helpful ! We could not be happier with our daughter’s wedding weekend at Great Oak Manor. Stunning gorgeous memorable

  Great Oak Manor is the perfect wedding venue ! Everything in the Manor is beautifully appointed. The grounds are gorgeous , the rooms beautiful and the staff so very pleasant and helpful ! We could not be happier with our daughter’s wedding weekend at Great Oak Manor. Stunning gorgeous memorable

  Great Oak Manor's reply:

  Thank you very much for your kind words and glowing review. WE appreciated the opportunity to host you, your family and your guests. Wonderful weekend.
• Melissa B. Sent on 01/13/2019
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  Planning a March wedding for Great Oak Manor

  We are planning our wedding at Great Oak Manor for this March and Holly has been fabulous, super accommodating and helpful! We are doing a small, family wedding and the venue is beautiful, well maintained and spacious while still being very affordable.

  We are planning our wedding at Great Oak Manor for this March and Holly has been fabulous, super accommodating and helpful! We are doing a small, family wedding and the venue is beautiful, well maintained and spacious while still being very affordable.
• Morgan Sent on 01/02/2019
  5 out of 5 rating

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  Beautiful Venue and Incredible Innkeepers!

  We celebrated our wedding weekend with Great Oak on the weekend of November 3rd, 2018 and it was absolutely amazing! When we started looking at wedding venues I knew I wanted somewhere with an incredible view of the bay and somewhere where we could stay all weekend with our friends and family which Great Oak checked off these boxes for us! Great Oak was our first venue tour and after touring a few other similar venues we just knew Great Oak was the perfect fit for us! Holly and Richard really sold us on the beautiful property not to mention Holly was just so nice and assured us that we would have the most beautiful wedding there! We booked them a year in advance since they book up fast and throughout the year of planning if we ever wanted to stop by or had any questions Holly was always there for us every step of the way! During our wedding weekend Holly and Richard made it the beat weekend of our lives! They made sure everything went smoothly and that if we needed anything at all they made sure we had it! All of our guests had a great time and they were definitely a huge part in making our wedding the wedding of our dreams! My only recommendation for Great Oak for future couples is I hope they are open to other vendors for tents for example Price Rentals instead of Eastern Shore Tents & Events. Eastern Shore Tents & Events are the most expensive around and we didn’t have the greatest experience with them. But other then that everything went perfectly and since we live locally we will definitely be back to visit Great Oak in the future! Thanks again from Davey and Morgan Eason!

  We celebrated our wedding weekend with Great Oak on the weekend of November 3rd, 2018 and it was absolutely amazing! When we started looking at wedding venues I knew I wanted somewhere with an incredible view of the bay and somewhere where we could stay all weekend with our friends and family which Great Oak checked off these boxes for us! Great Oak was our first venue tour and after touring a few other similar venues we just knew Great Oak was the perfect fit for us! Holly and Richard really sold us on the beautiful property not to mention Holly was just so nice and assured us that we would have the most beautiful wedding there! We booked them a year in advance since they book up fast and throughout the year of planning if we ever wanted to stop by or had any questions Holly was always there for us every step of the way! During our wedding weekend Holly and Richard made it the beat weekend of our lives! They made sure everything went smoothly and that if we needed anything at all they made sure we had it! All of our guests had a great time and they were definitely a huge part in making our wedding the wedding of our dreams! My only recommendation for Great Oak for future couples is I hope they are open to other vendors for tents for example Price Rentals instead of Eastern Shore Tents & Events. Eastern Shore Tents & Events are the most expensive around and we didn’t have the greatest experience with them. But other then that everything went perfectly and since we live locally we will definitely be back to visit Great Oak in the future! Thanks again from Davey and Morgan Eason!

  • +7 photos

  Great Oak Manor's reply:

  Thank you Davey and Morgan. You both were a dream to work with. No problems there. We look forward to seeing you around in the future and you are always welcome at the Manor anytime. Hugs,
  Holly
• Kara Sent on 06/18/2018
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  We just had our wedding and Great Oak and couldn't have asked for a better experience! The staff at Great Oak, Holly and Cass in particular, were amazing to work with from the beginning throughout the entire planning process. Chestertown is small and all of the vendors know each other. Great Oak has a great reputation and everyone jumped at the chance to work with Holly when I mentioned where our wedding was!
  
  I always got quick responses to my emails, someone always answered the phone when I called, and there was never a question the team couldn't answer for me. It made me feel reassured and comfortable that my venue was reliable and had true professionals working there.
  
  The venue itself is lovely. We rented out the entire house so it was filled with all of our family and friends. For the bride and groom - we stayed in the Carriage House which was an experience in itself. There was lots of hanging out on the outdoor patios, walks on the beach, and kayaks on the bay. It really is a perfect mixture of garden and beach and a fun time for all of those involved!
  
  All of our guests raved about the experience, the food (since breakfast is served each morning), the staff, and said it was one of the most beautiful weddings they'd ever seen.
  
  I couldn't agree more! Thank you Great Oak!

  We just had our wedding and Great Oak and couldn't have asked for a better experience! The staff at Great Oak, Holly and Cass in particular, were amazing to work with from the beginning throughout the entire planning process. Chestertown is small and all of the vendors know each other. Great Oak has a great reputation and everyone jumped at the chance to work with Holly when I mentioned where our wedding was!
  
  I always got quick responses to my emails, someone always answered the phone when I called, and there was never a question the team couldn't answer for me. It made me feel reassured and comfortable that my venue was reliable and had true professionals working there.
  
  The venue itself is lovely. We rented out the entire house so it was filled with all of our family and friends. For the bride and groom - we stayed in the Carriage House which was an experience in itself. There was lots of hanging out on the outdoor patios, walks on the beach, and kayaks on the bay. It really is a perfect mixture of garden and beach and a fun time for all of those involved!
  
  All of our guests raved about the experience, the food (since breakfast is served each morning), the staff, and said it was one of the most beautiful weddings they'd ever seen.
  
  I couldn't agree more! Thank you Great Oak!

  Great Oak Manor's reply:

  Thank you Kara and Kyle. We loved having you and your family and friends here. We wish you a wonderful life full of happiness and good health..
• Maryn Sent on 10/19/2017
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  Great Oak Manor is a dream wedding venue. The manor is timeless and beautiful (carriage house is awesome!), views and sunsets incredible, and staff especially Lynne was amazing. There are more picture spots here than you could possibly do. It was great to have the manor for the whole weekend which allowed us to set up everything before hand and made it a whole wedding weekend event. We had some bumps in the road communicating at first, but everything was sorted out. The new innkeepers seem to really know what they're doing. You have to see this place to believe it!

  Great Oak Manor is a dream wedding venue. The manor is timeless and beautiful (carriage house is awesome!), views and sunsets incredible, and staff especially Lynne was amazing. There are more picture spots here than you could possibly do. It was great to have the manor for the whole weekend which allowed us to set up everything before hand and made it a whole wedding weekend event. We had some bumps in the road communicating at first, but everything was sorted out. The new innkeepers seem to really know what they're doing. You have to see this place to believe it!

  Great Oak Manor's reply:

  Maryn, thank you very much for your great review. It was our pleasure hosting your special day.
  Holly
• Jess Sent on 04/25/2018
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  I would highly recommend Great Oak to any couple as the site for their wedding. We chose Great Oak Manor because it was the most unique venue we visited. The grounds are beautiful and the architecture is exquisite, which is great for guests and also for photos. We were married here in mid September 2017, and it was picture perfect. We had a very positive experience working with Holly, Jenn and their staff leading up to our wedding day and they helped to make the entire weekend easy. On our walkthrough we scoped out both the outdoor ceremony, reception areas and a back up indoor plan for inclement weather. I was impressed at how many people the venue could hold and loved that the grounds were sprawled out so guest have plenty of space. There’s a small beach, gazebo, bayside overlook, a wooded area, and separate private area with flat ground where we could have an outdoor reception and set up a massive sail cloth tent that we rented from Eastern Shore Tents and Events. What’s nice is the grounds are a blank canvas so you can customize it to your vision. I was also impressed by how well prepared the staff was when it came to advice. For example, one of our vendors had added a generator to our contract but the staff at Great Oak reviewed the contract and let us know they had enough power supply so we would only need the generator if we wanted to have it on hand as a backup... great tip for saving money during the planning process. Since we rented the entire venue for the weekend Fri-Sun, the staff worked ahead of time to plan out breakfast options for our guests who were staying at the manor and helped planned a Sunday brunch open to our out of town guests. My husband and I didn’t have to lift a finger! Our actual wedding day was absolutely beautiful weather so we had the ceremony & reception outdoors. Our guests were blown away with how beautiful the manor was and keep saying they cant wait to come back as guests which makes me very happy! I highly recommend it!

  I would highly recommend Great Oak to any couple as the site for their wedding. We chose Great Oak Manor because it was the most unique venue we visited. The grounds are beautiful and the architecture is exquisite, which is great for guests and also for photos. We were married here in mid September 2017, and it was picture perfect. We had a very positive experience working with Holly, Jenn and their staff leading up to our wedding day and they helped to make the entire weekend easy. On our walkthrough we scoped out both the outdoor ceremony, reception areas and a back up indoor plan for inclement weather. I was impressed at how many people the venue could hold and loved that the grounds were sprawled out so guest have plenty of space. There’s a small beach, gazebo, bayside overlook, a wooded area, and separate private area with flat ground where we could have an outdoor reception and set up a massive sail cloth tent that we rented from Eastern Shore Tents and Events. What’s nice is the grounds are a blank canvas so you can customize it to your vision. I was also impressed by how well prepared the staff was when it came to advice. For example, one of our vendors had added a generator to our contract but the staff at Great Oak reviewed the contract and let us know they had enough power supply so we would only need the generator if we wanted to have it on hand as a backup... great tip for saving money during the planning process. Since we rented the entire venue for the weekend Fri-Sun, the staff worked ahead of time to plan out breakfast options for our guests who were staying at the manor and helped planned a Sunday brunch open to our out of town guests. My husband and I didn’t have to lift a finger! Our actual wedding day was absolutely beautiful weather so we had the ceremony & reception outdoors. Our guests were blown away with how beautiful the manor was and keep saying they cant wait to come back as guests which makes me very happy! I highly recommend it!

  Great Oak Manor's reply:

  Thank you Jess for this wonderful review of your experience with Great Oak Manor. We wish all the best to you and Erik.
• Sara Sent on 09/14/2018
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  We fell in love with Great Oak Manor at first sight and it only got better from there! Every staff member was so caring, thoughtful, helpful, and wanted to make our wedding as special as possible. They treated us like family and our family could have not been more impressed. They were the most incredible hosts for our wedding weekend!

  We fell in love with Great Oak Manor at first sight and it only got better from there! Every staff member was so caring, thoughtful, helpful, and wanted to make our wedding as special as possible. They treated us like family and our family could have not been more impressed. They were the most incredible hosts for our wedding weekend!

  Great Oak Manor's reply:

  Thank you Sara. It was our greatest pleasure to be chosen by you for your wedding and reception. We appreciate your kind words.
• 
  User2637239 Sent on 06/07/2016
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  This is the perfect venue for your dream wedding, whatever that may look like. We held an elegant ceremony on the bluff over looking the Chesapeake Bay followed by dinner and dancing under an expansive tent on the lawn. The following day was a celebration with additional family and friends with something for everyone. Lawn games, swimming, kayaking, paddleboard, hammocks, etc. A perfect location for a beautiful experience

  This is the perfect venue for your dream wedding, whatever that may look like. We held an elegant ceremony on the bluff over looking the Chesapeake Bay followed by dinner and dancing under an expansive tent on the lawn. The following day was a celebration with additional family and friends with something for everyone. Lawn games, swimming, kayaking, paddleboard, hammocks, etc. A perfect location for a beautiful experience

  Great Oak Manor's reply:

  Belatedly, thank you for your great review of using Great Oak Manor as your wedding venue. We are thrilled you had such a wonderful experience.
  Holly-Manager/Innkeeper
• Alissa Sent on 06/02/2016
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  Great Oak Manor is an absolutely amazing, gorgeous getaway! I recently had my wedding there in May 2016 and I couldn't be happier with EVERYTHING!! The manor is absolutely beautiful and the surrounding grounds are breathtaking! The manor house is situated right on the water, and the views are incredible! The innkeepers, Kaylin and Scott, are absolutely amazing people as well! They were attentive, helpful, thoughtful, hardworking, and helped with so many details of the wedding and made everything run so smoothly! Anything we needed, they were there to happily help! They are such gems! Great Oak is such a great place for all occasions...from a private relaxing getaway (which my husband and I have also done!), family reunion, vacation with friends, or a wedding...this place is the most beautiful setting for all of the above!! I can't wait to go back! :)

  Great Oak Manor is an absolutely amazing, gorgeous getaway! I recently had my wedding there in May 2016 and I couldn't be happier with EVERYTHING!! The manor is absolutely beautiful and the surrounding grounds are breathtaking! The manor house is situated right on the water, and the views are incredible! The innkeepers, Kaylin and Scott, are absolutely amazing people as well! They were attentive, helpful, thoughtful, hardworking, and helped with so many details of the wedding and made everything run so smoothly! Anything we needed, they were there to happily help! They are such gems! Great Oak is such a great place for all occasions...from a private relaxing getaway (which my husband and I have also done!), family reunion, vacation with friends, or a wedding...this place is the most beautiful setting for all of the above!! I can't wait to go back! :)

  Great Oak Manor's reply:

  Hi Alissa,
  Belatedly, please accept our thanks for your generous review of Great Oak Manor as your wedding venue. We hope you both will visit again soon.
  Best,
  Holly-Manager/Innkeeper
• Liz Sent on 02/28/2016
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  We are so pleased that we chose to celebrate our wedding at Great Oak Manor! Scott and Kaylin were very patient and open to all of our ideas for the big day throughout the whole planning process. We had a full house since all of the wedding party and family members were staying at Great Oak during the weekend, but Scott and Kaylin kept everything going smoothly. Since it was a winter wedding, there were always warm beverages, homemade pastries (Kaylin's chocolate chip banana bread is amazing!), and fires in the fireplaces. The house looked beautiful and was full of Christmas cheer. On the day of the wedding, Scott and Kaylin were very helpful and even checked on me a few times to make sure that I was staying hydrated and fed! They stayed up until all of the guests had gone home and everyone was ready for bed in case we needed anything. The brunch they made on Sunday morning was absolutely delicious, and everyone kept on going back to the table for more! Having our wedding weekend at Great Oak Manor was a dream come true for us. We highly recommend booking this venue for your wedding and/or reception. We can't wait to go back for a long weekend getaway!

  We are so pleased that we chose to celebrate our wedding at Great Oak Manor! Scott and Kaylin were very patient and open to all of our ideas for the big day throughout the whole planning process. We had a full house since all of the wedding party and family members were staying at Great Oak during the weekend, but Scott and Kaylin kept everything going smoothly. Since it was a winter wedding, there were always warm beverages, homemade pastries (Kaylin's chocolate chip banana bread is amazing!), and fires in the fireplaces. The house looked beautiful and was full of Christmas cheer. On the day of the wedding, Scott and Kaylin were very helpful and even checked on me a few times to make sure that I was staying hydrated and fed! They stayed up until all of the guests had gone home and everyone was ready for bed in case we needed anything. The brunch they made on Sunday morning was absolutely delicious, and everyone kept on going back to the table for more! Having our wedding weekend at Great Oak Manor was a dream come true for us. We highly recommend booking this venue for your wedding and/or reception. We can't wait to go back for a long weekend getaway!

  Great Oak Manor's reply:

  Liz, thank you so much for your kinds words. We were thrilled to be a part of your wedding weekend and hope that we could contribute in making is a special time for you as well as your family and friends. Your wedding was such a beautiful event with lots of love and laughter, we wish you and Jay all the best in your new adventures as a married couple and hope that you will come back and visit us sometime soon!
• Yvette Sent on 08/28/2013
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  Amazing place and people to work with. The place was beautiful, the view incredible. My day was perfect for me. The manor had a warm and elegant feel and very comfortable. Our guests enjoyed their time there too.
  
  The InnKeeper can guide you on all the resources you need to create your perfect day!

  Amazing place and people to work with. The place was beautiful, the view incredible. My day was perfect for me. The manor had a warm and elegant feel and very comfortable. Our guests enjoyed their time there too.
  
  The InnKeeper can guide you on all the resources you need to create your perfect day!

  Great Oak Manor's reply:

  Belatedly, thank you for your review. I am the new event manager for this past year and saw that your kind review was never responded to. We hope you will remember us and plan a visit soon.
  Best regards,
  Holly, Manager/Innkeeper
• Devan D. Sent on 01/23/2021
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  A dream elopement

  We had to re-plan our wedding at the last minute due to COVID, and Holly at Great Oak put together a dreamy elopement package for us. She even connected us with a local officiant, florist, hair stylist and makeup artist!
  
  You cannot go wrong with a wedding at Great Oak!

  We had to re-plan our wedding at the last minute due to COVID, and Holly at Great Oak put together a dreamy elopement package for us. She even connected us with a local officiant, florist, hair stylist and makeup artist!
  
  You cannot go wrong with a wedding at Great Oak!

  • +3 photos

  Great Oak Manor's reply:

  Thank you Devan. Helping you and your mother was fun for me as I know it was a rush for you. So sorry that so many brides have had their plans for their special day upended by a pandemic. We were pleased and proud to be able to help you.
• Sheree Sent on 11/28/2014
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  We had the most unforgettable wedding weekend at Great Oak Manor. We rented the manor for the weekend so our guests could stay onsite with us. The manor and grounds are a stunning wedding venue. Our ceremony was held outdoors overlooking the water and our reception under a tent next to the manor house. Friday night, we had our rehearsal dinner on the lawn and a bonfire/welcome party afterwards. Unfortunately, the electricity in the backyard was not working so there was no lighting for our guests and it was incredibly dark and hard to see where guests were going. I spent 30 minutes lighting candles, meant for the next day, to illuminate the backyard. On Saturday, we utilized the conservatory for the ladies to get their hair and makeup done. Perfect lighting! The ceremony and tented reception went well until a huge storm came through...we moved the party into the manor and kept the party going in the conservatory. Sunday morning, we had our farewell brunch in the conservatory. My husband and I really LOVED the venue and our guests were blown away by it too. The only thing I wish could be improved upon was knowing that the electricity would be out in the backyard or at least having the venue help me figure out how to illuminate the area for my guests since they knew I wanted to use the backyard on Friday night.

  We had the most unforgettable wedding weekend at Great Oak Manor. We rented the manor for the weekend so our guests could stay onsite with us. The manor and grounds are a stunning wedding venue. Our ceremony was held outdoors overlooking the water and our reception under a tent next to the manor house. Friday night, we had our rehearsal dinner on the lawn and a bonfire/welcome party afterwards. Unfortunately, the electricity in the backyard was not working so there was no lighting for our guests and it was incredibly dark and hard to see where guests were going. I spent 30 minutes lighting candles, meant for the next day, to illuminate the backyard. On Saturday, we utilized the conservatory for the ladies to get their hair and makeup done. Perfect lighting! The ceremony and tented reception went well until a huge storm came through...we moved the party into the manor and kept the party going in the conservatory. Sunday morning, we had our farewell brunch in the conservatory. My husband and I really LOVED the venue and our guests were blown away by it too. The only thing I wish could be improved upon was knowing that the electricity would be out in the backyard or at least having the venue help me figure out how to illuminate the area for my guests since they knew I wanted to use the backyard on Friday night.

  Great Oak Manor's reply:

  Hi Sheree,
  Belatedly, thank you for your review. You will be please to know that we have backyard lighting now. Please visit with us soon.
  
  Best regards,
  Holly-Manager/Innkeeper
• Kathryn Sent on 05/01/2018
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  Loved everything about Great Oak! My guests were SO impressed by how beautiful the views were and the building/venue. I had so many compliments on how memorable my wedding will be due to the awesome location. The other cool aspect was having everyone stay together over the two days, we got really great quality time with friends and family.
  Just be sure your guests are aware of how far out it is and provide directions ahead of time. We had some snags in the schedule due to people getting lost on their way out.

  Loved everything about Great Oak! My guests were SO impressed by how beautiful the views were and the building/venue. I had so many compliments on how memorable my wedding will be due to the awesome location. The other cool aspect was having everyone stay together over the two days, we got really great quality time with friends and family.
  Just be sure your guests are aware of how far out it is and provide directions ahead of time. We had some snags in the schedule due to people getting lost on their way out.
• Sara Sent on 02/15/2017
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  When I went to review this venue I was shocked when I saw 5 star reviews- but then I noticed a lot of the reviews mention "Scott & Kaylin" as the inn keepers- they were fired. I too met them when I first toured Great Oak and fell in love with the manor but months before my wedding I was called by the new management and was informed Scott and Kaylin were let go. This is where the mess began. I met with the new manager Mike who told me right off the bat that he "hates" weddings- what a thing to say to a bride & paying customer. He dissed Scott and Kaylin and basically acted like the contract they had given me was complete crap. He was very hard to establish a rapport with. Would take forever to answer emails and questions and really just put off the vibe that he could pretty much care less about our wedding. I was so stressed out leading up to our wedding and was getting zero help from Great Oak. As our wedding approached I would email to ask small questions about this and that and for what I was paying I expected more of "yes mam of course whatever you need" but instead got push back on every detail. I will say that on the weekend of the wedding I was happy with how the staff treated us and they did step up when it came to the event but I am rating them so low as the manager made the wedding planning experience so awful for me. It is a beautiful venue and B&B but if you're planning to get married here, better spend the extra money (if you have any after paying their ridiculous prices) on a really good wedding planner because you will get no help from the people at Great Oak.

  When I went to review this venue I was shocked when I saw 5 star reviews- but then I noticed a lot of the reviews mention "Scott & Kaylin" as the inn keepers- they were fired. I too met them when I first toured Great Oak and fell in love with the manor but months before my wedding I was called by the new management and was informed Scott and Kaylin were let go. This is where the mess began. I met with the new manager Mike who told me right off the bat that he "hates" weddings- what a thing to say to a bride & paying customer. He dissed Scott and Kaylin and basically acted like the contract they had given me was complete crap. He was very hard to establish a rapport with. Would take forever to answer emails and questions and really just put off the vibe that he could pretty much care less about our wedding. I was so stressed out leading up to our wedding and was getting zero help from Great Oak. As our wedding approached I would email to ask small questions about this and that and for what I was paying I expected more of "yes mam of course whatever you need" but instead got push back on every detail. I will say that on the weekend of the wedding I was happy with how the staff treated us and they did step up when it came to the event but I am rating them so low as the manager made the wedding planning experience so awful for me. It is a beautiful venue and B&B but if you're planning to get married here, better spend the extra money (if you have any after paying their ridiculous prices) on a really good wedding planner because you will get no help from the people at Great Oak.

  Great Oak Manor's reply:

  As the new Manager/Innkeeper of Great Oak Manor this past year, I am offering my apology for your very bad experience. All I can say is that none of that should have ever happened to you. The owners are horrified and want you to know that the manager at the time had medical issues and was not himself. Nevertheless, that is not a excuse but the reason .Please call me at 410-778-5943 as we wish to offer you a special deal.
  Best regards,
  Holly McKee, Manager/Innkeeper
• Juliana D. Sent on 09/09/2020
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  Proceed with Caution - Bad Faith Contracting

  In early July 2020 my fiance and I drove out to the Eastern Shore to tour wedding venues. We saw several but fell in love with Great Oak Manor ("GOM"). The manor and grounds are absolutely beautiful! Also, GOM allows pets and we have two pups that absolutely have to be a part of our special day. I was soooo relieved to have found our venue and we provided GOM with a $500 deposit to reserve our date. Holly, the innkeeper, emailed us the contract about a week or two later. The contract didn't have a force majeure clause (a clause that excuses performance of the contract for both parties if there is a pandemic/act of god/fire, etc.) or a rescheduling provision - so we asked Holly for GOM to supplement the contract with language they had used in the past. She requested that we draft language that we thought was "reasonable," so we did (we are both attorneys). We submitted the draft language to her within a week and waited OVER A MONTH for GOM's attorney to review the language and submit his or her suggested edits. The attorney completely deleted the language we drafted and included a force majeure clause that only benefited GOM (i.e., did not excuse performance for us - the client - if this pandemic is still ongoing) and permitted rescheduling (with a sizeable fee) only if the pandemic is the reason for the rescheduling. Also, GOM even RAISED the prices/fees for several items in the contract and required payment in full (we are talking close to 20k) 9 MONTHS BEFORE THE WEDDING DATE with no chance of a refund FOR ANY REASON WHATSOEVER. We were baffled and totally turned off to say the least. Not to mention, the delay in getting the revised contract caused a great strain on our ability to solidify our plans. When we attempted to further negotiate with GOM in good faith, we were basically told "this is our contract now - take it or leave it." Well, we left it and are now in a terrible position of trying to find a new venue for June 2021. As all of us brides know, planning a wedding is an emotional journey. Unfortunately, GOM's actions (or more like inactions) caused us great anguish and disappointment in what should be a joyous time preparing for our special day.

  In early July 2020 my fiance and I drove out to the Eastern Shore to tour wedding venues. We saw several but fell in love with Great Oak Manor ("GOM"). The manor and grounds are absolutely beautiful! Also, GOM allows pets and we have two pups that absolutely have to be a part of our special day. I was soooo relieved to have found our venue and we provided GOM with a $500 deposit to reserve our date. Holly, the innkeeper, emailed us the contract about a week or two later. The contract didn't have a force majeure clause (a clause that excuses performance of the contract for both parties if there is a pandemic/act of god/fire, etc.) or a rescheduling provision - so we asked Holly for GOM to supplement the contract with language they had used in the past. She requested that we draft language that we thought was "reasonable," so we did (we are both attorneys). We submitted the draft language to her within a week and waited OVER A MONTH for GOM's attorney to review the language and submit his or her suggested edits. The attorney completely deleted the language we drafted and included a force majeure clause that only benefited GOM (i.e., did not excuse performance for us - the client - if this pandemic is still ongoing) and permitted rescheduling (with a sizeable fee) only if the pandemic is the reason for the rescheduling. Also, GOM even RAISED the prices/fees for several items in the contract and required payment in full (we are talking close to 20k) 9 MONTHS BEFORE THE WEDDING DATE with no chance of a refund FOR ANY REASON WHATSOEVER. We were baffled and totally turned off to say the least. Not to mention, the delay in getting the revised contract caused a great strain on our ability to solidify our plans. When we attempted to further negotiate with GOM in good faith, we were basically told "this is our contract now - take it or leave it." Well, we left it and are now in a terrible position of trying to find a new venue for June 2021. As all of us brides know, planning a wedding is an emotional journey. Unfortunately, GOM's actions (or more like inactions) caused us great anguish and disappointment in what should be a joyous time preparing for our special day.

  Great Oak Manor's reply:

  
  We are so sorry we weren't able to reach an agreement and we wish you the very best as you are planning the details for your special day. We understand what a challenging and emotional time this is to be planning a wedding and have adjusted our contracts to provide flexibility for wedding couples while also protecting our business to ensure we are able to host brides for many years to come.
  

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