The Eastern Shore Hotels

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The Eastern Shore Hotels

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Brampton Bed & Breakfast Inn

  • $$$

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 mi south of downtown Chestertown, this mid-19th-century...

Great Oak Manor

  • $$$

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

Imperial Hotel

  • $

This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today it is a gathering center...

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, then a general store;...

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