Chestertown Bed and Breakfasts

  • This charming 1901 Colonial is an old-fashioned delight, set in the heart of historic Annapolis!

    Scotlaur Inn Bed & Breakfast

  • Where pure luxury meets timeless elegance, just a short stroll from Baltimore's Inner Harbor, Harbor East and Little Italy.

    1840s Carrollton Inn

  • Elegant 1845 manor located downtown between the harbor business district and Baltimore's cultural center.

    4 East Madison Inn

  • The charm of Fells Point and the romance of Celie's, makes it a local favorite.

    Celie's Waterfront Inn

 
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B&Bs in Chestertown

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  From $199

25227 Chestertown Road, Chestertown, Maryland
The epitome of pleasant living.
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  From $119

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

  From $165

1710 Love Point Road, P.O. Box 399, Stevensville, Maryland
Fabulous B&B on the Eastern Shore of Maryland. Water front, Pool, Hot tub, Exercise room. Call for Weddings & Special Events.
  From $85

165 Main Street, Annapolis, Maryland
This charming 1901 Colonial is an old-fashioned delight, set in the heart of historic Annapolis!
  From $139

1714 Thames Street, Baltimore, Maryland
The charm of Fells Point and the romance of Celie's, makes it a local favorite.
  From $150

50 Albemarle Street, Baltimore, Maryland
Where pure luxury meets timeless elegance, just a short stroll from Baltimore's Inner Harbor, Harbor East and Little Italy.
  From $185

4 East Madison Street, Baltimore, Maryland
Elegant 1845 manor located downtown between the harbor business district and Baltimore's cultural center.
  From $149

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.
  From $180

201 Prince George Street, Annapolis, Maryland
This stylish example of a grand English country house, situated among some of the finest historic homes of Annapolis!
  From $180

26 Randall Street, Annapolis, Maryland
Park and walk to everything during your stay at this delightful Victorian in historic Annapolis!
  From $179

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.
  From $125.00

1400 Greenspring Valley Road, Baltimore, Maryland
Escape to the serenity of a historic mansion surrounded by breathtaking gardens, celebrating 25 years of hospitality!
  From $139

637 Washington Boulevard, Baltimore, Maryland
A Green friendly, 18th century Federal style historic inn located in the heart of Baltimore City Maryland.
  From $135

2023 East Baltimore Street, Baltimore, Maryland
Baltimore Row House located in historic Butchers Hill, steps away from Patterson Park, Johns Hopkins Medical Center...
  From $160

2920 Elliott Street, Baltimore, Maryland
Upscale, contemporary bed & breakfast featured in Southern Living and USA Today.com!