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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
9–14 Aug
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4.94 out of 5 average rating, 391 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, 240 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 10 beds
21–26 Aug
5.0 out of 5 average rating, 49 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed
2–7 Aug
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds
15–20 Sept
4.97 out of 5 average rating, 172 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds
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
16–21 Aug
4.97 out of 5 average rating, 66 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, 140 reviews
Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds
10–15 Aug
Top 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
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 162 reviews
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed
7–12 Aug
4.72 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Greenwood Lake
Cabinessence -on Greenwood Lake, NY #34370
2 bedrooms, 3 beds
9–14 Aug
4.96 out of 5 average rating, 488 reviews
Guest favourite
Home in Warwick
Walk to Village Charm! Warwick Home Near Dining
4 bedrooms, 6 beds
2–7 Aug
4.93 out of 5 average rating, 15 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed
13–18 Sept
4.89 out of 5 average rating, 267 reviews
Top guest favourite
Flat in Woodbury
Maple Ridge Retreats Apt. A
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 84 reviews
Guest favourite
Guest house in Chester
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1 bedroom, 1 bed
1–6 Aug
4.95 out of 5 average rating, 20 reviews