Chestertown Bed and Breakfasts

  • The epitome of pleasant living.

    Brampton Bed and Breakfast Inn

  • Cozy 1947 Cape Cod home in a great location, only a 10-minute stroll to downtown Chestertown & a 15-minute walk to the water.

    Simply Bed & Bread

 
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B&Bs in Chestertown

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BRAMPTON BED AND BREAKFAST INN

25227 Chestertown Road, Chestertown, Maryland
The epitome of pleasant living.
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  From $99

SIMPLY BED & BREAD

208 Mt. Vernon Avenue, Chestertown, Maryland
Cozy 1947 Cape Cod home in a great location, only a 10-minute stroll to downtown Chestertown & a 15-minute walk to the water.

B&Bs in Towns near Chestertown

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  From $149

MOONLIGHT BAY INN AND MARINA

6002 Lawton Avenue, Rock Hall, Maryland
Inn and Marina on the shore of the beautiful Chesapeake Bay, located in the yachting capitol of the Eastern Shore.
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  From $179

INN AT HUNTINGFIELD CREEK

4928 Eastern Neck Road, Rock Hall, Maryland
Elegant waterfront farm-estate B&B in historic Kent Co. The perfect solution for the big city blues! Romantic getaways.