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:
  • ADA Accessible
  • Breakfast Available
  • Catering Available
  • Free Breakfast
  • Free Parking
  • Free WiFi
  • Group-Friendly
  • Meeting Facilities
  • Number of Rooms
    12
  • Weddings
Rated 5 by 983katinaw

May 27, 2025

983katinaw

A respite full of elegance and genuine warmth

Great Oak is a place of gracious hospitality, where the warmth of its welcome mirrors the kindness of the Chestertown community. We were treated with the utmost of kindnesses and received exactly...

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Rated 5 by Patricia P

May 07, 2025

Patricia P

An Unforgettable Oasis on the Chesapeake Bay

What an oasis on the Chesapeake Bay, where you can relax, restore, refresh, and renew. Great Oak Manor is guaranteed to soothe your soul. Absolutely gorgeous gathering rooms for your various moods...

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Rated 5 by Jimmie M

April 19, 2025

Jimmie M

Relax and Recharge at the Great Oak Manor

We had an outstanding stay at the Great Oak Manor. The property is extremely beautiful, relaxing, historic and romantic. The home and I do mean home is located on several lush green acres on a...

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TripAdvisor Traveller Rating

Rated  based on 716 reviews
based on 716 Reviews
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