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 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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Rated 5 by Veronica H

June 30, 2025

Veronica H

THE ELEGANT GREAT OAK MANOR EXPERIENCE

My recent stay at Great Oak Manor was outstanding in every way. The property is beautiful and the Manor itself is elegant. My room was spacious and beautifully appointed. The bed was the first...

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Rated 5 by owensdoretha

June 30, 2025

owensdoretha

An Enchanting Getaway

I thoroughly enjoyed my stay at Great Oak Manor. From arrival to departure, I was treated with great care and attentiveness. I was amazed by the beautiful decor and attention to detail. The rooms...

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TripAdvisor Traveller Rating

Rated  based on 727 reviews
based on 727 Reviews
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