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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Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (370)
The price is P3,860
P4,284 total
includes taxes & fees
Jul 13 - Jul 14
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.
Go beyond your typical stay in Chestertown
Top landmarks in Chestertown
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Learn more about Chestertown
Wander cobblestone streets lined with 18th-century buildings, soaking in the colonial atmosphere of this historic Chesapeake Bay town. Sail the Chester River on a traditional skipjack, then browse antique shops and art galleries along High Street.

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Check out the Chestertown hotels guests love right now

Hilton Garden Inn Baltimore/White Marsh
10/10 Excellent
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- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near Historical Society of Kent County Maryland
- Hotels near River Arts Chestertown
- Hotels near Wilmer Park
- Hotels near Garfield Center for the Arts at the Prince Theater
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