Maryland Bed & Breakfast Association

When you stay in a Chestertown, Maryland bed and breakfast, you will feel like you’re taking a trip back in time.This area, located in the Upper Eastern Shore region, was once a busy port for Colonial settlers. The history of the area has been well preserved. As you walk the quiet cobblestone streets, you will find many 18th century homes and churches that have been beautifully restored. There is much to see in Chestertown. Take a day to visit the wonderful antique stores, eclectic galleries, and fantastic restaurants. Home to Washington College, Chestertown is the perfect home base for exploring the Eastern Shore of Maryland.From delicious seafood to beautiful views and calming waterscapes, you will quickly fall in love with all that this area has to offer. With many lodging options in the Eastern Shore area, let the Maryland Bed & Breakfast Association help you find the perfect inn to make your time in Chestertown unforgettable.

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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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Brampton Bed and Breakfast Inn

This award winning Maryland Bed and Breakfast Inn is located just one mile outside of charming Chestertown on Maryland’s Eastern Shore. The inn blends the grand elegance of a historical estate with comfort¬†and modern amenities. The large guest rooms offer wood-burning fireplaces (used during the colder months) and glorious views. A freshly prepared, full a-la-carte¬†breakfast [read more]

Chestertown, Maryland 21620
Phone: 410-778-1860
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