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Search results; 311 homes in Chestertown

Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio, 2 beds, 1 private bathroom
19–24 Aug
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4.97 out of 5 average rating, 286 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
4.96 out of 5 average rating, 112 reviews, 3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
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Home in Chestertown
High Tide & Hound
4.98 out of 5 average rating, 86 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5.0 out of 5 average rating, 245 reviews, 5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
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Home in Chestertown
Charming Haven on High
4.96 out of 5 average rating, 70 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
4.98 out of 5 average rating, 183 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
5.0 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Aug
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
New place to stay, 4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
4.98 out of 5 average rating, 141 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
4.98 out of 5 average rating, 124 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Aug
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Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
5.0 out of 5 average rating, 149 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
4.99 out of 5 average rating, 139 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
4.98 out of 5 average rating, 66 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Aug
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
4.99 out of 5 average rating, 252 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
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Home in Chestertown
Still Waters River House
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 7 beds, 2 bathrooms
1–6 Sept
Guest favourite
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1 bathroom
1–6 Aug