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Search results; 311 homes in Chestertown

Top guest favourite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
3 bedrooms, 4 beds, 2 private bathrooms
27 Mar – 1 Apr
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4.94 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 294 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
4.97 out of 5 average rating, 102 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
21–26 Aug
4.86 out of 5 average rating, 196 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 249 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bathroom
8–13 Dec
4.99 out of 5 average rating, 253 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 143 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 152 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 189 reviews
Top guest favourite
Room in Millington
Guest Suite in a Victorian on the Chester River
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 317 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 bathrooms
20–25 Aug
4.98 out of 5 average rating, 125 reviews
Guest favourite
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
4.95 out of 5 average rating, 76 reviews
Top guest favourite
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews