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Hotels with free cancellation in Chestertown
Red Roof Inn & Suites Chestertown
Good
Comfortable hotel in Chestertown with free self-parking, daily housekeeping, and convenient amenities like free Wi-Fi and a lobby fireplace.
Elevator / Lift
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Comfort Inn & Suites Chestertown
Very good
Enjoy a seasonal outdoor pool and complimentary breakfast in the historical district of Chestertown.
Top rated
Pool
Free Parking
Non-Smoking Rooms
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Brampton 1860
Exceptional
Top rated
5-star
Free Parking
Non-Smoking Rooms
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House On The Hill - Historic Private Second Floor
Exceptional
Top rated
Air Conditioned
Free Parking
TV
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High Tide & Hound
Exceptional
Top rated
Pet Friendly
Air Conditioned
TV
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-
Charming Haven on High
Exceptional
Top rated
Air Conditioned
Free Parking
TV
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Refrigerator
Cable / Satellite TV
Fireplace
Garden
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Free Parking
TV
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Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Exceptional
Top rated
Pet Friendly
Sauna
Refrigerator
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exceptional
Top rated
Refrigerator
Coffee / Tea Maker
Cable / Satellite TV
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Cozy 3-bedroom home w/ Hot tub & firepit
Exceptional
Top rated
Air Conditioned
Free Parking
TV
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Waterfront historic district 1BR Apartment
Exceptional
Top rated
Air Conditioned
Free Parking
TV
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Newly restored apartment in the heart of Chestertown
Exceptional
Top rated
Refrigerator
TV
Coffee / Tea Maker
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River front cottage with private dock & water fun
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
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Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Historic Downtown Garden Oasis with Private Patio
Exceptional
Top rated
Air Conditioned
Free Parking
-
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NEW Chestertown Retreat
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
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In Town Chestertown Rancher (1 Block to College)
Exceptional
Top rated
Air Conditioned
Free Parking
TV
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Quiet, Shabby-chic home in downtown Chestertown
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
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Pet-friendly Home on Chester River w/ Dock!
Superb
Top rated
Free Parking
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