27 Hotels
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27 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
Inn at Perry Cabin
On 25 acres beside the Miles River, this luxury inn—operated by the world-renowned Orient Express Hotels group... Read More
Atlantic Hotel
This fully restored 1895 inn blends the taste of grand living with modern conveniences. Spacious, hardwood-flo... 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
Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
This 370-acre complex is the Eastern Shore's first full-service, year-round resort, and one that takes full ad... Read More
Imperial Hotel
This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today... Read More
Lighthouse Club Hotel
This elegant boutique hotel is a Chesapeake Bay lighthouse lookalike of quiet luxury, just blocks from the bus... Read More
Park Place
Filling a need for more affordable, family- and child-friendly accommodations, this small, multistory hotel on... Read More
The Inn at Osprey Point
On 30 lush acres along Swan Creek, this stately Colonial-era building welcomes guests with brick fireplaces an... Read More
The Lankford Hotel & Apartments
Opened in 1924, the Lankford is still owned by the family of the original owners. Many combinations of rooms i... 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
River House Inn
With its welcoming front porch, this Victorian home and its adjacent cottages are on two lovely acres on the b... 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
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