Christina S.
10/28/2025
We had an absolutely lovely anniversary weekend at Great Oak Manor! The service and hospitality were warm and attentive, the attention to detail could not be more spot on. Food was fantastic...
Great Oak Manor
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(37)
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10568 Cliff Rd
Chestertown, MD 21620
Located directly on the Chesapeake Bay, Great Oak Manor is a historic 12 acre waterfront bed and breakfast located 8 miles outside of downtown Chestertown, Maryland. We have 12 rooms and are also an ideal venue for events and weddings.
Also at this address
Reviews
4.537 reviews
Ebony H.
8/26/2023
My friends and I had the honor of being invited to a small dinner party hosted by the owner. From the moment we stepped foot onto the immaculate grounds to the end of a beautiful dinner, I was...
Hal K.
6/28/2025
The overwhelming number of 5-star reviews (645 as of June, 2025) in Trip Advisor incredibly high rating of Great Oak Manor, the amazing service and the feel you get from the photos online are all...
Melinda G.
7/30/2022
GREAT OAK MANOR...A MAGNIFICENT WEEKDAY RETREAT We are discerning international travelers with a penchant for a certain mix of understated luxury, authenticity, beauteous settings, environmental...
Cherie S.
8/26/2023
From the moment we walked into the establishment, we were generously greeted, given the history and a mini tour. We were told that they were making some changes, however from what we experienced...
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