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.
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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.

Location

10568 Cliff Rd
Chestertown MD 21620
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Contact

Local Phone:
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  • Catering Available
  • Free Breakfast
  • Free Parking
  • Free WiFi
  • Group Tour Rates Offered
  • Group-Friendly
  • Meeting Facilities
  • Number of Rooms
    12 plus 1 carriage house
  • Pet-Friendly
  • Weddings
Rated 5 by ShellyEd2020920

September 24, 2020

ShellyEd2020920

Dream 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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Rated 2 by corweller

September 24, 2020

corweller

Expectations 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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Rated 5 by heatherfK1706XS

September 23, 2020

heatherfK1706XS

Beautiful, 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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TripAdvisor Traveller Rating

Rated  based on 531 reviews
based on 531 Reviews
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