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Search results; Over 1,000 homes in Chester

Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 427 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, 246 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, 53 reviews
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 397 reviews
Guest favourite
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, 143 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, 177 reviews
Top guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 19 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, 68 reviews
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 20 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
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, 1.5 bathrooms
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, 4 bathrooms
17–22 Aug
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, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 164 reviews
Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Oct
Home in Port Jervis
The Grazing Acres Getaway by Echo Fields
3 bedrooms, 3 queen beds, 2 bathrooms
16–21 Aug
New place to stay
Guest favourite
Guest house in Chester
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1 bedroom, 1 bed, 1 bathroom
17–22 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 218 reviews
Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed, 1 bathroom
23–28 Aug
4.73 out of 5 average rating, 33 reviews
Flat in Middletown
The Columbus Hotel | The Residence Studio | 89-206
1 double bed, 1 bathroom
17–22 Aug