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Search results; Over 1,000 homes in Chester

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, 247 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, 55 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, 399 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, 179 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
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
22–27 Aug
4.97 out of 5 average rating, 69 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.96 out of 5 average rating, 431 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
25–30 Aug
4.9 out of 5 average rating, 21 reviews
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
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 bathrooms
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, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
6–11 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Cabin in Greenwood Lake
Cabinessence -on Greenwood Lake, NY #34370
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Nov
4.96 out of 5 average rating, 493 reviews
Top guest favourite
Guest house in Woodbury
The Simplicity of the Experience.
1 bedroom, 2 beds, 1 bathroom
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, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 3 reviews