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.
Number of Rooms: 12 plus 1 carriage house
Catering Available
Free Breakfast
Free Parking
Free WiFi
Meeting Facilities



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TripAdvisor® Traveler Reviews

TripAdvisor Reviews
TripAdvisor Traveler Rating Based on 432 reviews
TripAdvisor Reviews
February 20, 2019
Our first visit to Great Oak was in 2004 and we immediately fell in love with the place, returning every year at least once, often several times, for a few days at a time. Over the years we've seen...
TripAdvisor Reviews
February 18, 2019
What a beautiful place! Holly and her husband Richard the innkeepers are welcoming, and kind. From the beautiful rooms to the scrumptious breakfast. It was more than we expected. We will be back...
TripAdvisor Reviews
February 17, 2019
Great Oak Manor is absolutely beautiful! From the moment we entered the grounds we knew we had chosen a truly special place to stay. This amazing estate has been perfectly maintained. We had a...