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Search results; 310 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 private bathroom
2–7 Nov
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4.99 out of 5 average rating, 251 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds
16–21 Aug
4.97 out of 5 average rating, 286 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds
23–28 Aug
4.96 out of 5 average rating, 112 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds
2–7 Aug
4.98 out of 5 average rating, 85 reviews
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
25–30 Aug
5.0 out of 5 average rating, 244 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds
2–7 Aug
4.96 out of 5 average rating, 69 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds
15–20 Aug
4.98 out of 5 average rating, 181 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds
10–15 Sept
5.0 out of 5 average rating, 96 reviews
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Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 15 reviews
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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 5 reviews
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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds
2–7 Aug
4.98 out of 5 average rating, 141 reviews
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Home in Chestertown
Still Waters River House
4 bedrooms, 7 beds
1–6 Sept
5.0 out of 5 average rating, 9 reviews
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds
1–6 Aug
4.98 out of 5 average rating, 123 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds
10–15 Aug
4.99 out of 5 average rating, 138 reviews
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds
1–6 Aug
5.0 out of 5 average rating, 60 reviews
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds
10–15 Aug
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Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 105 reviews
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Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds
1–6 Aug
5.0 out of 5 average rating, 6 reviews
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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds
11–16 Aug
4.96 out of 5 average rating, 139 reviews