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Search results; Over 1,000 homes in Chester

Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds, 1 private bathroom
11–16 Oct
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4.97 out of 5 average rating, 186 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 59 reviews
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
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 406 reviews
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, 169 reviews
Top guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 251 reviews
Top guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 70 reviews
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, 434 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 47 reviews
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
8–13 Sept
4.94 out of 5 average rating, 17 reviews
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
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
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
Home in Washingtonville
Beautiful home away from home
4 bedrooms, 6 beds, 4 bathrooms
9–14 Sept
New place to stay
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, 112 reviews
Home in Monroe
3 bd Home Near Legoland, West Point & Shopping
3 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.76 out of 5 average rating, 41 reviews
Top guest favourite
Room in Hamptonburgh
Hudson Haven, Blue Room
2 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Chester
Month2Month. 5 min Legoland
7 bedrooms, 9 beds, 4 bathrooms
8–13 Sept
4.75 out of 5 average rating, 4 reviews