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Historic Elegance on Maryland’s Eastern Shore!

Built in 1938 as a private residence for Russell D’Oenche, the Georgian-style Great Oak Manor is an experience in elegance you won’t soon forget! Unwind in one of 12 gracious period-themed guest rooms featuring private baths, balconies with Chesapeake Bay views, and replica antiques. And, make sure to roam the beautifully manicured lawns, enjoy a delicious breakfast in the Bayview Dining Room, or sip on tea in the music room. Pinkies up!

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 12 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Chestertown
  • Nearby Water N/A
  • Open Dates All Year


Born out of the bricks from the ballast of W.R. Grace sailing ships, Great Oak Manor was styled after an 18th-century English country retreat. It's name is believed to refer to a large oak tree that once marked one of the corners of the property.


You and your loved one will love cuddling next to the cozy fireplace of The Marmaduke room. Or, if you're feel especially romantic, the Manor's Eastern Shore setting makes for a dramatic and picture-perfect wedding!


Arrange a luxurious one-hour massage right in your room for only $75!

  • Whirlpool
  • Shopping
  • Sightseeing
  • Swimming
  • Tennis
  • Beach
  • Beach
  • Wildlife & Nature
  • Meeting Room(s)
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Nearest Airports

  • Phillips Army Air Field (APG) / 13.8 miles
  • Baltimore/Washington International Thurgood Marshal Airport (BWI) / 25.7 miles
  • Lee Airport (ANP) / 29.8 miles

* Not all airports listed here may be open to public use, or service commercial flights

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