Chestertown, Maryland Bed and Breakfast Inns

We currently have 5 Chestertown bed and breakfast inns. In addition to top quality inns such as Claddaugh Farm B & B and Brampton Inn, we have nearby bed and breakfasts in the cities and towns of Saint Michaels, Annapolis and Rock Hall. See the Nearby Cities list on the right to find the perfect bed and breakfast near Chestertown, Maryland.

Recommended Chestertown Bed & Breakfasts

Brampton Inn Has photosHas ratings
The Brampton Bed & Breakfast is one of the finest inns on Maryland's Eastern Shore. Built in 1860 as a...

Claddaugh Farm B & B
Claddaugh Farm B & B is a bed and breakfast inn located in the Chestertown area. This Maryland B&B is run by Melissa and Michael Hollis who can be reached at (410) 778-4894....

Great Oak Manor Bed and Breakfast Has photosHas ratings
Overlooking the Chesapeake Bay on Maryland's Eastern Shore, Great Oak is a real find for anyone searching for that...

Imperial Hotel
The Imperial is a unique building with a distinctive double veranda over the front entrance. The guest rooms are individually...

Lauretum Inn
Lauretum (1881) sits splendidly atop a tree graced knoll on six acres in Chestertown, MD. A long winding lane invites...

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