16 Hotels
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16 Hotels
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Brampton Bed & Breakfast Inn
On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 miles south of downtown Chesterto... Read More
Combsberry
This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias an... Read More
Great Oak Manor
On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century... Read More
Imperial Hotel
This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today... Read More
The Oaks, a Country Inn
Antebellum grace defines this 1748 mansion on 17 acres along the banks of Oak Creek, 3 miles from St. Michaels... Read More
White Swan Tavern
Step back in time at this inn restored to its appearance circa 1790. Built as a home in 1733, it was a tavern,... Read More
Bartlett Pear Inn
Natives Jordan and Alice Lloyd returned to their hometown and bought a 220-year-old home (the former Inn at Ea... Read More
Elk Forge B&B Inn and Retreat
A 20-minute drive from North East, Elk Forge is nestled among 5 acres of woods and gardens along Big Elk Creek... Read More
Five Gables Inn & Spa
Three circa-1860 houses have been turned into an elegant and comfortable getaway. All rooms have a private por... Read More
Lodgecliffe on the Choptank
Located on a rise overlooking the river, this elegant turn-of-the-20th-century country home was the first bed-... Read More
Robert Morris Inn
In the early 1700s this building on the banks of the Tred Avon River was crafted as a home by ships' carpenter... Read More
Ship Watch Inn
Three levels of broad decks mean that every room has a place from which to relax and watch all manner of water... Read More
Tilghman Island Inn
Warm and welcoming conviviality and casual elegance define this compact, modern resort overlooking the Chesape... Read More
Victoriana Inn
Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War ar... Read More
Inn of Silent Music
Located in a town that's separated by water from the other two villages on Smith Island, this remote English c... Read More
Kent Manor Inn
A summer hotel since 1898, this imposing antebellum manor house is on 226 acres of farmland along Thompson Cre... Read More
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