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

Chestertown, MD
21620

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Contact

US Toll Free: 800-504-3098

Map

Eastern Shore

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

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.

February 02, 2026

cnt1977

Perfect getaway!

This was an absolutely incredible stay. The hotel is beautiful and clean. The food was delicious and the staff was top notch. They went above and beyond! I loved my stay.

February 02, 2026

Natashia D

Heavenly

Heavenly. The snow, the geese, the warmth of the fireplaces burning inside. The friendly and attentive staff, the cozy room and especially the views. It felt like living inside a great holiday movie...