Weekend Getaway: Great Oak Manor

This Maryland B&B is the perfect trip for a quiet escape.



Great Oak Manor
10568 Cliff Road, Chestertown, Md., (410) 778-5943

Cost: Weekdays $159-$249, weekends $200-$299.

Drive time: 1 hour, 30 minutes.

The scoop: Set on Maryland’s Upper Eastern Shore, this 18th-century country-style B&B was built in 1938. Its 12 rooms are decorated with antique reproductions, and some rooms offer water views.  

Amenities: In addition to breakfast, complimentary cruiser bikes, kayaks, canoes and paddleboards are available. Guests also have private beach access and may utilize the amenities of the marina, including a swimming pool, a nine-hole golf course, and tennis courts. Dog-friendly rooms are available.      

Don’t miss: Five months after Boston Harbor turned into a “tea party,” a group of like-minded men did the same in Maryland’s Chester River. That event is commemorated every Memorial Day Weekend with the townwide Chestertown Tea Party Festival. Activities include foot races, a street fair and much more. 

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