If you're looking for a place to get away, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.
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Hotels in Chestertown
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Where to stay in Chestertown?

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (335)
The price is CA $80
CA $89 total
includes taxes & fees
Mar 23 - Mar 24
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top landmarks in Chestertown
Washington College
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
Learn more about Chestertown
Notable for its university life, Chestertown features attractions such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. The city has something for everyone including sights like Garfield Center for the Arts at the Prince Theater and Urieville Lake Fish Management Area within a small-town setting.

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Open Photo by Assya A
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- Hotels near Baltimore Cruise Terminal
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- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
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