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 Chesapeak...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, Exerc...Read more
 
 
from $175

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

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