Chestertown Bed and Breakfasts

Chestertown is located on the banks of the Chester River, on the upper eastern shore of Maryland, and it is home to many cozy B\u0026B establishments. In May, Chestertown...  Read more
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B&Bs in Chestertown

from $139

Chestertown, MD
Within city limits
A palatial 1700's style Georgian Manor set on 12 acres overlooking the Chesapeake Bay on ...Read more

B&Bs in Towns near Chestertown

from $179

Stevensville, MD
Fabulous B&B on the Eastern Shore of Maryland. Water front, Pool, Hot tub, Exercise room....Read more
from $250

Easton, MD
Welcome To Your Own Private Guest House! Take in a deep breath, drink in the view....Read more
from $175

Rock Hall, MD
Elegant waterfront farm-estate B&B in historic Kent Co. The perfect solution for the big ...Read more
from $160

Rock Hall, MD
Inn and Marina on the shore of the beautiful Chesapeake Bay, located in the yachting capi...Read more