Maryland Bed & Breakfast Association

The Eastern Shore was given its name by Captain John Smith, who sailed from Jamestown in the summer of 1608 to explore the Chesapeake Bay as far north as the Sassafras River. Kent Island was one of the initial settlements starting about 1631, and for three hundred years thereafter, the Eastern Shore has thrived on its agricultural and seafood base, and prided itself on its distinct and independent ways.

The coastline is dotted with historic waterfront towns and rolling farmlands where fresh and salt water meet for fishing and boating enthusiasts, cyclists, birders, and nature lovers. A bike ride through the rural landscape may take you to Chestertown, where you can rent a kayak to paddle the Chester River for a chance to see a great blue heron, an osprey, or an eagle. For more bird watching, visit The Eastern Neck National Wildlife Refuge.

The fishing, crabbing, and sailing town of Rock Hall is known for its seafood restaurants and natural wildlife preserves. Visit The Rock Hall Museum or Waterman's Museum to learn more about oystering and crabbing.

Take day trips to Annapolis and Baltimore and know that the welcoming hospitality of the innkeepers at our Maryland Bed and Breakfast Association member inns awaits you after a busy day.

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Inn at Huntingfield Creek

The Inn at Huntingfield Creek in Rock Hall, Maryland, is situated on the oldest land grant in Kent Co. Once a 1200 acre estate, it is now 70 pristine acres with gorgeous shoreline on Huntingfield Inlet. The well-appointed, comfortable rooms offer luxurious amenities and wonderful beds. Soothing, harmonious decor. Pet/family- friendly cottages, saltwater pool, charming [read more]

Rock Hall, Maryland 21661
Phone: 410 639-7779
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Great Oak Manor Bed and Breakfast

American Historic Inns list of America’s most Romantic Inns, featured on the Today show, and situated on a bluff overlooking the majestic Chesapeake Bay on Maryland’s Eastern Shore, Great Oak Manor offers romantic getaways with eleven luxurious guest rooms, all with private baths and king beds, seven with water views and five with working fireplaces. [read more]

Chestertown, Maryland 21620
Phone: 410-778-5943
Toll Free: 800-504-3098
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Crow Farmstay B&B

Unique lodging at Crow Farmstay B&B, a bed and breakfast inn located on a 365 acre farm in Kennedyville, Maryland. Enjoy modern amenities within a primitive farm charm. About an hours’ drive from Baltimore, Washington D.C., Philadelphia, Wilmington and minutes from historic Chestertown on Maryland’s Eastern Shore…so there’s plenty to do when you stay at Crow [read more]

Kennedyville, Maryland 21645
Phone: (410)648-5687
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