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 a... Read moret 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!

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.

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

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

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 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... Read more 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 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... Read more 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 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!

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... Read more 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!

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!

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

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 su... Read morebmit 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.

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.