Chestertown Holidays
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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.
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
Plenty of parking, various items for breakfast, family friendly, close to many location
Reviewed on 12 May 2026
Red Roof Inn & Suites Chestertown
Clean lady was nice help me out
Reviewed on 26 Apr 2026
The Lodge at Great Oak Landing
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...
Reviewed on 23 Apr 2026
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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.
