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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, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 399 reviews
Top guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed
23–28 Aug
4.95 out of 5 average rating, 246 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds
21–26 Aug
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 179 reviews
Guest favourite
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, 143 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds
20–25 Aug
4.97 out of 5 average rating, 69 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed
25–30 Aug
4.9 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds
6–11 Sept
4.96 out of 5 average rating, 431 reviews
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds
26–31 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds
7–12 Sept
4.98 out of 5 average rating, 162 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds
29 Aug – 3 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
6–11 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds
7–12 Sept
4.92 out of 5 average rating, 167 reviews
Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds
23–28 Aug
4.98 out of 5 average rating, 83 reviews
Guest favourite
Place to stay in Monroe
A-Frame Modern House w/ Private Pond
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Guest house in Woodbury
The Simplicity of the Experience.
1 bedroom, 2 beds
13–18 Sept
5.0 out of 5 average rating, 20 reviews
Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds
2–7 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Room in Middletown
Charming Upstate New York Inn Cozy Suite #102
1 queen bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews