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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
30 Aug – 4 Sept
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4.94 out of 5 average rating, 397 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, 54 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
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, 178 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 431 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
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
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
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
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 20 beds, 4.5 bathrooms
20–25 Aug
New place to stay
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
Guest favourite
Place to stay in Monroe
A-Frame Modern House w/ Private Pond
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 60 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 Monroe
3 BDR Cottage (Hudson Valley Cottage)
3 bedrooms, 3 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 63 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, 19 reviews
Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 337 reviews
Top guest favourite
Cottage in Florida
Family Stay: Legoland & Wine Country Living!
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 65 reviews