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
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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 Paulette B

March 14, 2026

Paulette B

10/10 Would Highly Recommend

Great Oak Manor is an absolute gem and place I would highly recommend. From the moment you arrive, you’re surrounded by breathtaking views, warm hospitality, and a peaceful atmosphere that instantly...

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Rated 5 by Lindsey P

March 02, 2026

Lindsey P

A happy writers retreat

I spent 4 wonderful days at the Manor, on a writers conference. The incredibly kind staff, the accommodations were 5 star, the food was so thoughtfully made and fantastic and the entire atmosphere...

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Rated 5 by Sherialaw

February 13, 2026

Sherialaw

An amazing escape with all the positive trappings of home

An absolute oasis that feels like home with better appointments and service. I cannot say enough to laud the accommodations, food, and drink. An ideal location for a retreat.

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TripAdvisor Traveller Rating

Rated  based on 742 reviews
based on 742 Reviews
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