Great Oak Manor

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: Christian Giannelli Photography
Built in 1938, this 12,000 square-foot Georgian-style estate with private beach access offers 12 spacious guest rooms, including pet friendly options, two outdoor firepits, cruiser bicycles, kayaks, paddleboards, and a delicious full breakfast included in your stay. Experience carefree "elegance on the bay" at our waterfront Chestertown, Maryland bed and breakfast and event venue.
Catering Available
Free Parking
Group Tour Rates Offered



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TripAdvisor® Traveler Reviews

TripAdvisor Reviews
TripAdvisor Traveler Rating Based on 465 reviews
TripAdvisor Reviews
May 18, 2020
We had a great experience at the Great Oak. The wedding was handled beautifully and the staff was amazing. Stunning place and amazing views. We will definitely be back each year to celebrate our...
TripAdvisor Reviews
May 18, 2020
Holly Richard and joe make each guest feel special. The sunsets and views of thebay are worthy he price of admission. Many of the rooms have new carpeting and furnishings and the grounds are well...
TripAdvisor Reviews
May 18, 2020
My husband and I stayed at Great Oak Manor for two nights. We were getting our boat ready to launch at a nearby marina. Holly, the Inn keeper, was so accommodating. Our room was beautiful with a view...