Chestertown Holidays from £749
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Your Chestertown Holiday
There's no better way to embark on an adventure than with one of our holiday packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Centre for the Arts at the Prince Theatre, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown holiday on Expedia.
Top Chestertown Flight + Hotel Deals
The Lodge at Great Oak Landing
Reviewed on 16 Jun 2026
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,100 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Historical Society of Kent County Maryland, Garfield Centre for the Arts at the Prince Theatre and Crow Farm and Vineyard |
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."
Reviewed on 14 Jun 2026
Red Roof Inn & Suites Chestertown
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."
Reviewed on 22 Jun 2026
The Lodge at Great Oak Landing
"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."
Reviewed on 16 Jun 2026
Stay near popular Chestertown attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
