Great Oak Manor
Built in 1938, this 12,000 square-foot Georgian-style estate with private beach access offers 12 spacious guest rooms, including pet friendly options, two outdoor firepits, cruiser bicycles, kayaks, paddleboards, and a delicious full breakfast included in your stay. Experience carefree "elegance on the bay" at our waterfront Chestertown, Maryland bed and breakfast and event venue.
Built in 1938, this 12,000 square-foot Georgian-style estate with private beach access offers 12 spacious guest rooms, including pet friendly options, two outdoor firepits, cruiser bicycles, kayaks, paddleboards, and a delicious full breakfast included in your stay. Experience carefree "elegance on the bay" at our waterfront Chestertown, Maryland bed and breakfast and event venue.
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September 24, 2020
ShellyEd2020920Dream Come True!
As was true for so many brides during this difficult year of 2020, our daughter’s dream of a large, elegant, September wedding, surrounded by her family and friends, was dashed due to attendance size...
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September 24, 2020
corwellerExpectations were too high
This was supposed to be a romantic getaway for my girlfriend and I after 9 months of planning and anticipation. Perhaps that was our fault, as the quality was less than expected. The first thing that...
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September 23, 2020
heatherfK1706XSBeautiful, relaxing, and serene place!
My husband & I stumbled across Great Oak Manor while searching online for a bed & breakfast on the water in Maryland. What a gem! Lovely “old” home with an abundance of character and class. Holly...
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