Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620 Get Directions 
Phone: 410-778-5943
Toll Free: 800-504-3098
Great Oak Manor Inn exterior view at night
Photo Credit: Great Oak Manor Inn
Built in 1938, this Georgian style estate covers 12,000 square-feet of grounds. Carefree "elegance on the bay." Nine acres of beauty with beach access and your getaway is sure to be remembered.
Catering Available
Free Parking
Group Tour Rates Offered



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TripAdvisor Reviews
TripAdvisor Traveler Rating Based on 420 reviews
TripAdvisor Reviews
October 28, 2018
Annie M
The Great Oak Manor is a beautiful estate. The landscape is beautiful, the views of the bay are incredible. Holly and Richard are super sweet and super helpful. We were away for a long weekend...
TripAdvisor Reviews
October 27, 2018
Great Oak Manor was the perfect place for a girls' get away. When I called to make a reservation, the person at the reception desk took a lot of time to help us choose the "best" rooms. The staff...
TripAdvisor Reviews
October 22, 2018
This B&B is a select registry choice. I have stayed at their choices of B&B’s before. I must say the standard for this B&B are quit disappointing. My husband and I were celebrating our 23rd wedding...