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 Lola A

February 04, 2025

Lola A

Absolutely stunning!

Great Oak Manor is a gorgeous and intricately designed boutique manor with 12 stunningly crafted rooms, lots of fireplaces, libraries, nooks, and crannies for you to create, read, relax, and simply...

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Rated 5 by MissOPJ

November 12, 2024

MissOPJ

A little slice of heaven….

This Inn is the perfect hideaway for couples, a solo traveler and group retreats. From the moment I pulled up to the Great Oak Manor the smiles, the service, the food, the beautiful grounds, all...

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Rated 5 by Roy L

November 03, 2024

Roy L

Place of Peace, Beauty and Tranquility

This is such a great location to disconnect from the world to re-focus and re-center yourself. The grounds are beautiful, the staff is absolutely pleasant and I had a wonderful weekend experience...

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TripAdvisor Traveller Rating

Rated  based on 708 reviews
based on 708 Reviews
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