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.


Brampton Bed and Breakfast Inn Brampton Bed and Breakfast Inn
25227 Chestertown Road
Chestertown, MD 21620
866-305-1860 | 410-778-1860
Distance 1 miles.
Crow Farmstay B&B Crow Farmstay B&B
12441 Vansants Corner Road
Kennedyville, MD 21654
Distance 13 miles.
Great Oak Manor Bed and Breakfast Great Oak Manor Bed and Breakfast
10568 Cliff Road
Chestertown, MD 21620
800-504-3098 | 410-778-5943
Distance 8 miles.
Moonlight Bay Inn Moonlight Bay Inn
6002 Lawton ave
Rock Hall, Maryland 21661
(410)639 2660
Distance 12 miles.
Inn at Huntingfield Creek Inn at Huntingfield Creek
4928 Eastern Neck Rd
Rock Hall, Maryland 21661
410 639-7779
Distance 13 miles.