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. Vacation home rentals area also available in the Chestertown area.

Chestertown Lodging Map


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.  Book online direct or Call Now: 877-926-0076 for the Best Price Guarantee.

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.

Chestertown Bed & Breakfasts

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