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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
4–9 Oct
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4.94 out of 5 average rating, 408 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 252 reviews
Superhost
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 bathrooms
11–16 Sept
4.92 out of 5 average rating, 170 reviews
Guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
11–16 Sept
4.97 out of 5 average rating, 70 reviews
Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 186 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 434 reviews
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
11–16 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 47 reviews
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 163 reviews
Top guest favourite
Home in Chester
Sunshine Adventures - 5bd Hudson Valley Escape
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 54 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed, 1 bathroom
13–18 Sept
4.73 out of 5 average rating, 33 reviews
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.94 out of 5 average rating, 95 reviews
Guest favourite
Home in Monroe
3 BDR Cottage (Hudson Valley Cottage)
3 bedrooms, 3 queen beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 66 reviews
Guest favourite
Home in Warwick
Warwick Retreat | Fire Pit | Wineries | Sleeps 8
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.88 out of 5 average rating, 43 reviews
Top guest favourite
Home in Goshen
Unique Dutch Barn in the Hudson Valley
5 bedrooms, 9 beds, 3 bathrooms
11–16 Sept
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 14 reviews