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Search results; Over 1,000 homes in Chester

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Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 private bathrooms
6–11 Sept
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4.85 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
7–14 Sept
5.0 out of 5 average rating, 57 reviews
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Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
7 bedrooms, 20 beds, 5 bathrooms
27 Sept – 2 Oct
4.86 out of 5 average rating, 145 reviews
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Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 405 reviews
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Top guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 249 reviews
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Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 184 reviews
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Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 70 reviews
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Guest favourite
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 bathrooms
11–16 Sept
4.92 out of 5 average rating, 167 reviews
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Top guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 433 reviews
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Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
6–11 Sept
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 163 reviews
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Guest favourite
Home in Chester
Sunshine Adventures - 5bd Hudson Valley Escape
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 52 reviews
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Home in Washingtonville
Beautiful home away from home
4 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
New place to stay
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Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 23 reviews
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Top guest favourite
Flat in Goshen
Carriage House Apartment Close to Legoland NY
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Goshen
Historic Hudson Valley Farm House
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 110 reviews
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Guest suite in Monroe
Relax at the Green Home
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 4 reviews