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Search results; Over 1,000 homes in Chester

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Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 private bathrooms
26–31 Oct
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4.98 out of 5 average rating, 164 reviews
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Guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 253 reviews
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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
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Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 411 reviews
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Guest favourite
Flat in Chester
Private Country Getaway
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 188 reviews
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Superhost
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds, 2 bathrooms
18–23 Oct
4.92 out of 5 average rating, 170 reviews
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Guest favourite
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 435 reviews
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Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 71 reviews
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Superhost
Room in Chester
En suite Bathroom 40 min-Mt. Creek (Shared House)
1 bed, 1 bathroom
17–22 Sept
4.73 out of 5 average rating, 33 reviews
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Superhost
Home in Chester
Woodland Retreat in KJ, Monroe & Chester!
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
New place to stay
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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
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Guest favourite
Home in Chester
Comfy house near lakes, hikes and RenFair
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest suite in Warwick
The Wine House - Private Parking
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 144 reviews
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Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
4.89 out of 5 average rating, 418 reviews
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Guest favourite
Guest house in Chester
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.95 out of 5 average rating, 22 reviews