filters

Search results; 322 homes in Chestertown

Home in Chestertown
Quiet, Shabby-chic home in downtown Chestertown
2 bedrooms, 2 beds, 2 private baths
Aug 21–26
,
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bath
Aug 29–Sep 3
4.97 out of 5 average rating, 291 reviews
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed, 1 bath
Aug 16–21
4.86 out of 5 average rating, 196 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 baths
Sep 6–11
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bath
Aug 17–22
4.99 out of 5 average rating, 252 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 baths
Aug 15–20
4.98 out of 5 average rating, 186 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bath
Aug 25–30
4.99 out of 5 average rating, 141 reviews
Top guest favourite
Guesthouse in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bath
Aug 13–18
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 baths
Aug 30–Sep 4
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 baths
Aug 20–25
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bath
Aug 22–27
4.97 out of 5 average rating, 102 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 baths
Aug 13–18
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bath
Aug 27–Sep 1
5.0 out of 5 average rating, 151 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 baths
Aug 20–25
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 baths
Aug 30–Sep 4
4.96 out of 5 average rating, 115 reviews
Top guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bath
Aug 22–27
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bath
Aug 30–Sep 4
4.92 out of 5 average rating, 189 reviews
Top guest favourite
Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 baths
Aug 16–21
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bath
Aug 23–28
4.98 out of 5 average rating, 142 reviews