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Search results; Over 1,000 homes in Chester

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Top guest favourite
Home in Chester
Sunshine Adventures - 5bd Hudson Valley Escape
5 bedrooms, 6 beds, 3 shared bathrooms
27 Sept – 2 Oct
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4.94 out of 5 average rating, 54 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, 146 reviews
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Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
19–25 Oct
5.0 out of 5 average rating, 59 reviews
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Guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 254 reviews
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Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 411 reviews
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Superhost
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 bathrooms
18–23 Oct
4.92 out of 5 average rating, 170 reviews
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Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds, 1 bathroom
23–28 Oct
4.97 out of 5 average rating, 188 reviews
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Guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Sept
4.84 out of 5 average rating, 50 reviews
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Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 435 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
26 Sept – 1 Oct
4.97 out of 5 average rating, 71 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
8–13 Oct
4.95 out of 5 average rating, 19 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, 165 reviews
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Top guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 24 reviews
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Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed, 1 bathroom
27 Sept – 2 Oct
4.73 out of 5 average rating, 33 reviews
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Guest favourite
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, 5 reviews
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Superhost
Home in Chester
Woodland Retreat in KJ, Monroe & Chester!
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
New place to stay
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Guest favourite
Home in Monroe
3 BDR Cottage (Hudson Valley Cottage)
3 bedrooms, 3 queen beds, 1 bathroom
12–17 Oct
4.93 out of 5 average rating, 67 reviews
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Superhost
Home in Chester
Month2Month. 5 min Legoland
7 bedrooms, 9 beds, 4 bathrooms
20–25 Sept
4.75 out of 5 average rating, 4 reviews