Why results appear this way
Show total price
Top rated hotels in Chestertown
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
-
-
Brampton 1860
Exceptional
Top rated
5-star
Free Parking
Non-Smoking Rooms
-
-
House On The Hill - Historic Private Second Floor
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
High Tide & Hound
Exceptional
Top rated
Pet Friendly
Air Conditioned
TV
-
-
Charming Haven on High
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Exceptional
Top rated
Pet Friendly
Sauna
Refrigerator
-
-
Cozy 3-bedroom home w/ Hot tub & firepit
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Waterfront historic district 1BR Apartment
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Newly restored apartment in the heart of Chestertown
Exceptional
Top rated
Refrigerator
TV
Coffee / Tea Maker
-
-
River front cottage with private dock & water fun
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
-
-
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
-
-
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exceptional
Top rated
Refrigerator
Coffee / Tea Maker
Cable / Satellite TV
-
-
NEW Chestertown Retreat
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
-
-
In Town Chestertown Rancher (1 Block to College)
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Quiet, Shabby-chic home in downtown Chestertown
Exceptional
Top rated
Pet Friendly
Air Conditioned
Free Parking
-
-
Pet-friendly Home on Chester River w/ Dock!
Superb
Top rated
Free Parking
-
-
Walk to Historic Chestertown: Dog-friendly Retreat
Exceptional
Top rated
-
-
Waterfront Retreat with Private Dock and Beach
Exceptional
Top rated
Air Conditioned
Free Parking
TV
-
-
Great Oak Manor
Superb
Top rated
Air Conditioned
Garden
-
-
