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
ChestertownMD21620
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Contact
US Toll Free:
  • ADA Accessible
  • Breakfast Available
  • Catering Available
  • Free Breakfast
  • Free Parking
  • Free WiFi
  • Group-Friendly
  • Meeting Facilities
  • Number of Rooms
    12
  • Weddings
Rated 5 by Jimmie M

April 19, 2025

Jimmie M

Relax and Recharge at the Great Oak Manor

We had an outstanding stay at the Great Oak Manor. The property is extremely beautiful, relaxing, historic and romantic. The home and I do mean home is located on several lush green acres on a...

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Rated 5 by JanineBosley

April 12, 2025

JanineBosley

Perfect comfort in an idyllic get-away setting.

This was our third stay at Great Oak Manor. Once again, the place (with its beautiful new lounge areas and luxurious room/suite appointments), the setting and the staff (who bring it all together...

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Rated 5 by mwimes

April 01, 2025

mwimes

Great Oak Manor--An exquisite way to spend your downtime!

I have been attending a women's retreat at Great Oak Manor for the past four years. Every time I step into the front foyer, I feel like I can exhale. The calming, relaxing and inviting environment...

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TripAdvisor Traveller Rating

Rated  based on 713 reviews
based on 713 Reviews
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