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Inns in Chestertown

A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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Cheap Inns in Chestertown

Historic Waterfront Kent Manor Inn

500 Kent Manor Dr Stevensville MD

Stay at this inn in Stevensville. Popular attractions Northern Chesapeake Bay and Paul Reed Smith Guitars are located nearby.

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See all 1,100 properties in Chestertown

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 Trending Hotels in Chestertown

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...

8/10 Very Good! (122 reviews)

"Cool spot by a marina. House felt clean and good beds."

Reviewed on Oct 17, 2026

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Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...

7.2/10 Good! (510 reviews)

"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."

Reviewed on Oct 15, 2026

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Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

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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.