The Eastern Shore Travel Guide

4 Hotels

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4 Hotels

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1

Brampton Bed & Breakfast Inn

$$$ | Chestertown 25227 Chestertown Rd.

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

B&B/Inn


2

Great Oak Manor

$$$ | Chestertown 10568 Cliff Rd.

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

B&B/Inn


3

White Swan Tavern

$$ | Chestertown 231 High St.

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


4

Imperial Hotel

$ | Chestertown 208 High St.

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

B&B/Inn

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