Great Oak Manor

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10568 Cliff Rd.
Chestertown, MD 21620

(410) 778-5943 or (800) 504-3098

This elegant 12 room waterfront manor house will enchant you with gorgeous sunsets over the Chesapeake Bay on Maryland’s Eastern Shore. Twelve acres of waterfront, private beach access, hammocks, Adirondack chairs, kayaks and bikes are available. Located just 8.5 miles from Chestertown and an hour from Baltimore, Washington D.C., and Philadelphia.

While staying at our pet-friendly inn on Maryland’s Eastern Shore, we invite you to take advantage of our luxurious accommodations. Guests enjoy a full breakfast in the Bay View Dining Room. Explore our common areas – read one of the many books in the Library or relax in the Sunroom and drink a glass of wine after visiting the area’s fabulous wineries. Indulge daily in a sweet and savory afternoon snack, and nap in the hammocks or Adirondack chairs on the bluff. When you return from dinner, look forward to the complimentary Port and Sherry in the Music Room. Every Friday enjoy Manager’s Wine & Cheese Hour.


Nearby Wineries:

Great Oak Manor Wineries

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