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

 
 
Starting
at $189

Chestertown, Maryland
Our Maryland bed and breakfast is perfect for your romantic getaway with hammocks for two...Read more
 
 
Starting
at $119

Chestertown, Maryland
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

 
 
Starting
at $165

Stevensville, Maryland
Fabulous B&B on the Eastern Shore of Maryland. Water front, Pool, Hot tub, Exercise room....Read more
 
Starting
at $150

St. Michaels, Maryland
Country Serenity - Bay Splendor...Read more
 
Starting
at $185

Baltimore, Maryland
Elegant 1845 manor located downtown between the harbor business district and Baltimore's ...Read more
 
Starting
at $150

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

Rock Hall, Maryland
Inn and Marina on the shore of the beautiful Chesapeake Bay, located in the yachting capi...Read more
 
Starting
at $179

Rock Hall, Maryland
Elegant waterfront farm-estate B&B in historic Kent Co. The perfect solution for the big ...Read more
 
Starting
at $125

Baltimore, Maryland
Escape to the serenity of a historic mansion surrounded by breathtaking gardens, celebrat...Read more