We just spent a delightful weekend at the Great Oak Manor Inn. Cass and John, the innkeepers, treated us as special guests. We enjoyed the beautiful view of the Chesapeake Bay; each breafast was scrumptious and different; suggestions for activities, exploring, and good restaurants always proved excellent; each of the downstairs rooms offered an invitation to sit and relax; our... more

My bicycle group stayed here and Sally and I weren't able to make it with them. The rave reviews were too much, so we planned our own trip. We totally enjoyed our time there. more

My husband and I celebrated my birthday with a two night stay at Great Oak Manor on the Chesapeake Bay, just outside of one of our favorite small towns, Chestertown, MD.. It was a perfect get-away, with beautiful accomodations in a manor house with a rich history. The service was fabulous, including delicious breakfasts each day served in a to-die-for... more

It hasn't even been an entire year since we last visited the Great Oak Manor in Chestertown, MD when we received an email from Cassandra, the Innkeeper, inviting us back with a special offer letting us have two nights for the price of one. We've been wanting to go back to the Manor to begin with for so long, but... more

Our bicycling group of ten reserved 5 rooms at the Inn and we were blown away with the Inn. It is in a beautiful setting just outside Chestertown, MD. We were biking in the area and wanted a quiet place to stay that would allow us to gather for social times after riding. The Inn has beautiful grounds, patios to... more

Our family stayed for one week and celebrated our daughter's wedding there. It was just perfect. We have gotten so many compliments from our guests saying it was the best wedding ever - we certainly believe so. Our hosts John & Cassandra and their staff could not do enough for us - make sure you ask for Charlie. The rooms... more

I was very impressed with my overall experience at the Great Oak Manor. The house is absolutely beautiful, the grounds are breathtaking and the owners Cassandra and John are most hospitable. The staff is warm, friendly and accommodating as well. We were at the Great Oak Manor for my cousins wedding and took over the Inn with family and friends.... more

We arrived at this charming and secluded bed and breakfast inn on the first of three consecutive rainy days. On our first morning, we asked the owner what he'd recommend we do on a rainy day. "Stay here!" he said with enthusiasm. "It's a manor house and you don't get to stay in a place like this very often, so... more

My wife and I aren't usually impressed by luxury and pampering, but this vacation was one of those times where we really needed some down time and a nice place to spend it. The Great Oak Manor really delivered on all counts for us. We reserved The Tilden Room which is on the second floor with an awesome view of... more