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 JP1532

August 24, 2025

JP1532

Perfection on the Bay

We have been visiting Great Oak Manor for many years, attracted by the beautiful setting and proximity to the Chesapeake Bay. So we are fans of this venue, for sure. But I must say that over the...

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Rated 5 by Angela S

August 22, 2025

Angela S

Amazing stay

We really enjoyed our stay at the Manor. The manor was absolutely beautiful which was decorated nicely with stunning views especially sunset views. Many outside amenities of which we took advantage...

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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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TripAdvisor Traveller Rating

Rated  based on 731 reviews
based on 731 Reviews
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