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Search results; 310 homes in Chestertown

Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio, 2 beds, 1 private bathroom
4–9 Oct
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4.97 out of 5 average rating, 298 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
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 252 reviews
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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
20–25 Sept
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
13–18 Nov
5.0 out of 5 average rating, 153 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 70 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 194 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, 202 reviews
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Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
12–17 Oct
4.86 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Chestertown
RIVER WATCH
3 bedrooms, 3 queen beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 121 reviews
Top guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 143 reviews
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.92 out of 5 average rating, 191 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 126 reviews
Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 118 reviews
Guest favourite
Guest house in Chestertown
Piney Grove 2 Bedroom Carriage House Apartment
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.98 out of 5 average rating, 53 reviews