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10568 Cliff Rd, Chestertown, MD 21620
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Phone Number(410) 778-5943

Set on Maryland's stunning Eastern Shore, Great Oak Manor is as rich in charm as it is in history.


Built in 1938, this 12,000 square foot manor was once a private residence, built from bricks that once adorned a historic sailing ship. Styled after an 18th century English country retreat, it now offers the ideal place for those couples who want to embark on a peaceful romantic mid-Atlantic escape.


Great Oak Manor features 12 rooms featuring their own unique decor and individual highlights.


You might find yourself curled up in front of your own cozy fireplace, or relaxing in the spacious bath gazing at the stars through the skylight. Perhaps you would rather stroll through the garden via the inviting French doors.


Every morning is not only met with stunning views of the Chesapeake Bay, but guests are also treated to a full breakfast with seasonal fresh fruit, homemade baked goods, cold cereal, and a hot entrée, such as delicious French toast, or quiches.


Feel free to enjoy your breakfast in the dining room, or take it out to the terrace to enjoy as the sun rises along the Eastern Shore.


Great Oak Manor provides more than a place to sleep. It's location on the Chesapeake Bay in Chestertown surrounds you with that magical waterfront energy. Take advantage of the amenities that the manor offers to really make the most of your adventure.


Cruiser bikes, canoes, kayaks and paddleboards are all available, and they even have private beach access from the manor itself. At night, relax by the waterside firepit and just watch the stars come out above you.


Where the magic of the English countryside and charming mid-Atlantic join forces to give you that romantic Maryland escape you will be itching to return to the minute you leave.


You can use some of the amenities of the marina next door including the pool, fitness room and golf course but just bring your own gear.


They have three designated pet-friendly rooms: the Sterling, Roese and the Caulk Suites, with a $25 pet fee - just let them know ahead of time



- Historic

- Breakfast Included

- Fireplace

- Ocean Views

- Firepit

- Outdoor Activities

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