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Search results; 398 places in Chestertown

Guest favorite
Home in Chestertown
Simple Living on the Pond
2 queen beds
Apr 29 – May 4
4.93 out of 5 average rating, 73 reviews
Guest favorite
Home in Chestertown
Pet friendly, historic house, near town center.
6 beds
Jun 16 – 21
5.0 out of 5 average rating, 154 reviews
Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Apr 28 – May 3
5.0 out of 5 average rating, 67 reviews
Guest favorite
Room in Chestertown
Stay with Sarah And AndrewIt,
House On The Hill - Historic Private Second Floor
Apr 28 – May 3
4.98 out of 5 average rating, 44 reviews
Guest favorite
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
Apr 28 – May 3
4.98 out of 5 average rating, 41 reviews
Guest favorite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
Apr 20 – 25
4.93 out of 5 average rating, 46 reviews
Guest favorite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Apr 30 – May 5
4.99 out of 5 average rating, 130 reviews
Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Jun 24 – 29
4.99 out of 5 average rating, 191 reviews
Guest favorite
Apartment in Chestertown
Quiet, pet frienly, escape in center of town
1 king bed
May 5 – 10
4.97 out of 5 average rating, 193 reviews
Guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
May 5 – 10
5.0 out of 5 average rating, 45 reviews
Guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
Apr 30 – May 5
4.96 out of 5 average rating, 71 reviews
Guest favorite
Barn in Chestertown
Pet friendly, romantic hideaway, downtown location
1 king bed
Apr 21 – 26
4.96 out of 5 average rating, 25 reviews
Guest favorite
Home in Chestertown
125 High - Luxury Historical Brick Victorian
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 24 reviews
Guest favorite
Home in Chestertown
Lovely, Recently-Renovated Home in Chestertown
4 beds
May 11 – 16
5.0 out of 5 average rating, 50 reviews
Guest favorite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
8 beds
Apr 21 – 26
4.99 out of 5 average rating, 149 reviews
Guest favorite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
5 beds
Apr 20 – 25
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Chestertown
Magnolia House ~Historic Downtown w/Private Garden
4 beds
Apr 20 – 25
5.0 out of 5 average rating, 24 reviews
Guest favorite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
Apr 20 – 25
5.0 out of 5 average rating, 75 reviews