The Eastern Shore Hotels

Outside of Cambridge's singular Hyatt Regency and Ocean City's approximately 10,000 hotel rooms—the great majority of accommodations throughout this region a... Read More

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1. Brampton Bed & Breakfast Inn

$$$ | 25227 Chestertown Rd., Rte. 20 W, Chestertown, Maryland, 21620-3944, United States

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 mi south of downtown Chestertown,... Read More

2. Great Oak Manor

$$$ | 10568 Cliff Rd., Chestertown, Maryland, 21620-4115, United States

On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century... Read More

3. Imperial Hotel

$ | 208 High St., Chestertown, Maryland, 21620-1518, United States

This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today... Read More

4. White Swan Tavern

$$ | 231 High St., Chestertown, Maryland, 21620-1517, United States

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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