Great Oak Manor

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

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: 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

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...

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...

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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