Great Oak Manor is a newly renovated 12-room Georgian-style luxury boutique hotel located on an oasis of stately trees and expansive lawn on Chesapeake Bay a few miles from the quaint village of Chestertown in Kent County on Maryland's Eastern Shore.
Hours See website for hours.
Location
10568 Cliff Rd
Chestertown, MD
21620
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Contact
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  • ADA Accessible
  • Breakfast Available
  • Catering Available
  • Free Breakfast
  • Free Parking
  • Free WiFi
  • Group-Friendly
  • Meeting Facilities
  • Number of Rooms
    12
  • Weddings
Rated 5 by joshuai526

August 11, 2025

joshuai526

Excellent place.

We enjoyed our stay here in the Geddes room, which was comfortable and quiet. The grounds are very pretty and peaceful, with a great sunset view, and chairs down on the bay beach for morning coffee...

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Rated 5 by Richard T

July 21, 2025

Richard T

Fantastic B&B Resort on the Chesapeake Bay.

Fantastic Historic Mansion. Wonderful, attentive staff. Decorated as a Mansion of this Stature should be decorated. Waterfront views and private beach. We stayed Thursday through Sunday and could...

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Rated 5 by alehotzky

July 08, 2025

alehotzky

Enjoyable place of solitude

From the moment we walked into Great Oak Manor, we were impressed with the house, the rooms and the grounds. The views of the Chesapeake as well as the sunset were beautiful. Everyone we came in...

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TripAdvisor Traveller Rating

Rated  based on 729 reviews
based on 729 Reviews
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