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Search results; Over 1,000 homes in Chester

Superhost
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.92 out of 5 average rating, 170 reviews
Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
7 bedrooms, 20 beds
27 Sept – 2 Oct
4.86 out of 5 average rating, 145 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds
4–9 Oct
4.94 out of 5 average rating, 410 reviews
Guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.95 out of 5 average rating, 253 reviews
Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds
11–16 Oct
4.97 out of 5 average rating, 187 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 70 reviews
Guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds
11–16 Oct
4.96 out of 5 average rating, 435 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds
20–25 Sept
4.85 out of 5 average rating, 47 reviews
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds
26–31 Oct
4.98 out of 5 average rating, 164 reviews
Top guest favourite
Home in Chester
Sunshine Adventures - 5bd Hudson Valley Escape
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 54 reviews
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds
8–13 Oct
4.72 out of 5 average rating, 18 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed
20–25 Sept
4.92 out of 5 average rating, 24 reviews
Home in Washingtonville
Beautiful home away from home
4 bedrooms, 6 beds
20–25 Sept
New place to stay
Guest favourite
Home in Monroe
3 BDR Cottage (Hudson Valley Cottage)
3 bedrooms, 3 queen beds
20–25 Sept
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Home in Goshen
Unique Dutch Barn in the Hudson Valley
5 bedrooms, 9 beds
20–25 Sept
4.97 out of 5 average rating, 116 reviews
Guest favourite
Home in Warwick
Warwick Retreat | Fire Pit | Wineries | Sleeps 8
4 bedrooms, 6 beds
4–9 Oct
4.88 out of 5 average rating, 43 reviews
Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed
15–20 Sept
4.73 out of 5 average rating, 33 reviews