Chestertown Hotels

Chestertown is in Maryland's Eastern Shore. Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. When staying in Chestertown, we recommend Holiday Inn Express Hotel and Suites Chestertown, Comfort Suites Chestertown, Driftwood Inn, and Moonlight Bay Marina and Inn (12 miles south).

Chestertown Hotels and Accommodation

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Recommended Chestertown Hotels

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Holiday Inn Express Hotel and Suites Chestertown ★★
150 Scheeler Road, Chestertown, Maryland
Rated 9/10 by 91 reviews
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Comfort Suites Chestertown ★★★
160 Scheeler Rd., Chestertown, Maryland
Rated 8.8/10 by 23 reviews
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Driftwood Inn ★★
609 Washington Avenue, Chestertown, Maryland
Rated 6/10 by 8 reviews
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Moonlight Bay Marina and Inn
6002 Lawton Avenue, Rock Hall, Maryland (12 miles south)
Rated 7.3/10 by 10 reviews
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Our recommendations of Holiday Inn Express Hotel and Suites Chestertown, Comfort Suites Chestertown, Driftwood Inn, and Moonlight Bay Marina and Inn may take into account distance from Chestertown, guest ratings and accommodation popularity.

Chestertown Tourist Information

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