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
Get Directions
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 Dennis T

June 14, 2025

Dennis T

Very enjoyable stay

My wife and I truly enjoyed the great oak manor the staff was extremely friendly and helpful. The chef’s food was amazing we had a fabulous dinner and breakfast. We highly recommend staying here...

Read More
Rated 5 by William D

June 11, 2025

William D

Perfect weekend.

Staff was wonderful, food was delicious and room was perfect! Just what my fiancé and I needed. Chestertown is lovely as well, but one could spend the whole weekend on the property and be happy. We...

Read More
Rated 5 by Annemarie C

June 08, 2025

Annemarie C

Beautiful, Relaxing And Plenty of Amenities

My husband and I just spent two nights at the Great Oak Manor. It was our first visit and we will definitely return. Surrounded by so much beauty including the bay wth a private beach, it is a...

Read More

TripAdvisor Traveller Rating

Rated  based on 719 reviews
based on 719 Reviews
Read all the reviewsWrite a review

Restaurants and Attractions Nearby