Chestertown Vacation Packages
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Your Chestertown Vacation
There's no better way to embark on an adventure than with one of our vacation 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 Center for the Arts at the Prince Theater, 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 vacation on Expedia.
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
Traveling on 301 to New England somewhat off the beaten path Service excellent
Reviewed on Apr 28, 2026
Red Roof Inn & Suites Chestertown
Clean lady was nice help me out
Reviewed on Apr 26, 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 Apr 23, 2026
Discover the most popular places to visit in Chestertown
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
