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Search results; Over 1,000 homes in Chester

Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 394 reviews
Top guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 245 reviews
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, 174 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 52 reviews
Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed, 1 bathroom
9–14 Aug
4.73 out of 5 average rating, 33 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
11–16 Aug
4.94 out of 5 average rating, 17 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, 142 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 427 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 67 reviews
Superhost
Room in Middletown
Charming Upstate New York Inn Cozy Suite #102
1 queen bed, 1 bathroom
28 Aug – 2 Sept
New place to stay
Home in Chester
The Chester House • a wooded hilltop retreat
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Hamptonburgh
Hudson Haven, Blue Room
2 beds, 2 bathrooms
15–20 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 162 reviews
Top guest favourite
Cottage in Warwick
Ranch in the Woods | A Peaceful Designer Retreat
1 bedroom, 1 king bed, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 131 reviews
Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
9–14 Aug
4.93 out of 5 average rating, 15 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 47 reviews
Top guest favourite
Farm stay in High Falls
Dave's Milk Barn
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.88 out of 5 average rating, 1081 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 80 reviews