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 $189

Chestertown, MD
Within city limits
Our Maryland bed and breakfast is perfect for your romantic getaway with hammocks for two...Read more
from $119

Chestertown, MD
Within city limits
Cozy 1947 Cape Cod home in a great location, only a 10-minute stroll to downtown Chestert...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 $125

Baltimore, MD
Where pure luxury meets timeless elegance, just a short stroll from Baltimore's Inner Har...Read more
from $150

Rock Hall, MD
Inn and Marina on the shore of the beautiful Chesapeake Bay, located in the yachting capi...Read more
from $95

Baltimore, MD
Escape to the serenity of a historic mansion surrounded by breathtaking gardens, celebrat...Read more
from $185

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