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Search results; 304 homes in Chestertown

Guest favourite
Flat in Chestertown
1-br apt in downtown Chestertown (Unit 1)
1 bedroom, 1 bed, 1 private bathroom
28 Aug – 2 Sept
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4.91 out of 5 average rating, 98 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, 292 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, 91 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
17–22 Aug
4.86 out of 5 average rating, 196 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 141 reviews
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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
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, 188 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 102 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, 248 reviews
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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
Chestertown - Eastern Shore Getaway
1 bedroom, 1 king bed, 1 bathroom
1–6 Dec
4.98 out of 5 average rating, 200 reviews
Guest favourite
Guest house in Rock Hall
Carriage House
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.9 out of 5 average rating, 100 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
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
17–22 Aug
4.96 out of 5 average rating, 139 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 115 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, 151 reviews