Great Oak Manor

Name: Great Oak Manor
Address: 10568 Cliff Rd, Chestertown, MD, 21620, US
Telephone: 800-504-3098

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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.

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Location

10568 Cliff Rd

Chestertown MD 21620

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Contact

US Toll Free: 800-504-3098

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Eastern Shore

	ADA Accessible Breakfast Available Catering Available Free Breakfast Free Parking Free WiFi Group-Friendly Meeting Facilities Number of Rooms 12 Weddings

August 21, 2026

annaaU1608DQ

Outstanding two nights at the Lodge.

Absolutely top notch experience, from the outstanding room to the inviting grounds and beach! We enjoyed the three-course dinner (with wine pairing) both nights, it was two of the best meals we have...

August 11, 2026

Eryn C

Excellent Weekend Getaway- Attention to the Details

We spent a weekend away for our anniversary at Great Oaks and it was fabulous. The little details they think of to make your stay memorable are awesome and I LOVED the library and ability to borrow...

July 24, 2026

Carl N

Get away for birthday and unwind

My wife and I recently stayed at Great Oak Manor and had a fantastic time. The entire staff could not be more accommodating. From Corrine, to Sophie and especially Cameron, their attention to detail...

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