Chestertown Lodging

Chestertown Lodging

Chestertown Lodging Options


There are quite a few lodging options in the Chestertown area. Two chain hotels are located near town as well as several bed and breakfast establishments. There are some vacation rentals available in the area too.


Chestertown Hotels


Holiday Inn Express Hotel & Suites Chestertown – Located convenient to downtown and Washington College. Free high-speed internet.  Complementary buffet breakfast. Fitness center, indoor pool.  Compare rates & read traveler reviews.

Quality Suites Chestertown – Located one mile from historic downtown. Heated indoor pool.  Suites with refrigerator, microwave, and coffee maker. Convenient to Washington College. This property was formerly a Comfort Suites. Compare rates & read traveler reviews.


Chestertown Bed & Breakfasts


  • Brampton Bed & Breakfast Inn – Located on 20 wooded acres, just one mile outside of Chestertown, Maryland.   25227 Chestertown Road, Chestertown, MD  21620. 
  • Great Oak Manor Inn–  Waterfront bed and breakfast on the outskirts of Chestertown.  
  • The Inn at Mitchell House –  Located between Chestertown and Rock Hall in Kent County.  An 18th Century manor house on 12 manicured acres.
  • John Stam House – Four guest rooms in historic downtown Chestertown. 114 Washington Street, Chestertown, MD.
  • Simply Bed and Bread–  Located 100 yards from the Washington College campus and a 10 minute walk to downtown Chestertown.
  • Widow’s Walk Inn –  In Chestertown’s historic district.  Within walking distance of the Chester River, Washington College, shops and restaurants.
  • White Swan Tavern–  A restored historic inn. 

Chestertown Vacation Rentals

dock-two-chairsGet away for a while with a vacation home rental.  Whether you stay for a weekend or a week these home-away-from homes make a wonderful retreat. Choose a large home with lots of bedrooms and recreation area for a family reunion or gathering with friends or a cozy one bedroom cottage for a romantic weekend escape.

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This three bedroom house has a dock on the Chester River. Four kayaks provided for guest use.  More info

This two bedroom, 1 1/2 bath contemporary waterfront home is located less than 20 minutes from downtown Chestertown.  More info