10 Hotels
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10 Hotels
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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
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