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Escape to Great Oak Manor, a quaint Maryland bed and breakfast on the eastern shore, where the Chesapeake Bay
is aglow in warm sunsets; where towering Oaks gently
kiss the skyline; and where you can let your body rest and
your mind wander.
Tucked away on the outskirts of Chestertown, Maryland,
our magnificent 18th century country-style estate rests
alongside the waterfront. With 11
guestrooms, Great Oak offers the
finest in a romantic luxury bed and breakfast
inn, where all of your whims are
cared for, day and night.
Spend an afternoon perusing the
quaint streets of historic Chestertown, exploring the
Eastern Neck refuge, sampling the fresh catch in Rock Hall,
or just curl up in the arms of a weathered Adirondack chair
to soak up the view.
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Read Our Recent Blog Posts
About the Sassafras Sailing Excursions with Captain Wendy 06/26/2009
Hello Cassandra!
Thanks again for yet another wonderful stay in your lovely home! It hurt so bad to have to wake up in my own bed. I, of course, will get over it and will look forward to our next stay and visit with you and John as well as Charlie, Max and the rest of [...]
Great time at Great Oak Manor 06/11/2009
By: Tom Adkinson
Memorable hotel rooms have stories to tell. My room at Great Oak Manor on Maryland’s Eastern Shore once was a gambling den. Cool, very cool.
A previous owner, several decades before the place became the romantic bed and breakfast it is today, played fast and loose with the social conventions of kinder and gentler [...]
Bethanne Coples Plein Air Workshop | Great Oak Manor 05/21/2009
Hello everyone at South Street Gallery
 I attended Bethanne Cople’s Plein air workshop held in April. I procrastinated and registered just in time for the one remaining spot. I was apprehensive because I had never attended a workshop before.
I just wanted to let you know my expectations were far exceeded. The workshop was an exhilarating experience.
The [...]
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