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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
9–14 Aug
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4.96 out of 5 average rating, 427 reviews
Guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed
26–31 Jul
4.95 out of 5 average rating, 238 reviews
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds
9–14 Aug
4.94 out of 5 average rating, 389 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds
30 Jul – 4 Aug
5.0 out of 5 average rating, 47 reviews
Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds
15–20 Sept
4.97 out of 5 average rating, 167 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed
20–25 Jul
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds
17–22 Jul
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds
18–23 Jul
4.84 out of 5 average rating, 45 reviews
Guest favourite
Place to stay in Monroe
A-Frame Modern House w/ Private Pond
2 bedrooms, 3 beds
16–21 Aug
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds
30 Jul – 4 Aug
4.98 out of 5 average rating, 162 reviews
Guest favourite
Home in Monroe
3 BDR Cottage (Hudson Valley Cottage)
3 bedrooms, 3 queen beds
9–14 Aug
4.92 out of 5 average rating, 59 reviews
Guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds
13–18 Sept
4.91 out of 5 average rating, 328 reviews
Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
7 bedrooms, 20 beds
20–25 Sept
4.86 out of 5 average rating, 140 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds
26–31 Jul
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds
7–12 Sept
4.94 out of 5 average rating, 95 reviews
Top guest favourite
Cabin in West Milford
Luxury Lake AFrame • Hot Tub • Sauna • Game Room
2 bedrooms, 8 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 bedroom, 1 queen bed
2–7 Aug
4.96 out of 5 average rating, 25 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, 8 reviews
Guest favourite
Home in Monroe
NEW Luxury Lakefront Retreat | Pool, Boats & Games
4 bedrooms, 4 beds
12–17 Sept
5.0 out of 5 average rating, 8 reviews