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Search results; Over 1,000 homes in Chester

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Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds, 1 private bathroom
4–9 Oct
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4.94 out of 5 average rating, 410 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, 5 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
27 Sept – 2 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
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
29 Sept – 4 Oct
4.92 out of 5 average rating, 170 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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Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
8–13 Oct
4.72 out of 5 average rating, 18 reviews
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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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Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
4.85 out of 5 average rating, 48 reviews
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Guest favourite
Home in Warwick
Magnum Hilltop
4 bedrooms, 4 beds, 4 bathrooms
27 Sept – 2 Oct
4.86 out of 5 average rating, 21 reviews
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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, 164 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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Home in Monroe
Spacious 4BR Retreat | Legoland • Warwick • Trails
5 bedrooms, 7 beds, 2 bathrooms
21–26 Oct
New place to stay
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Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Warwick
Cozy Cabin Getaway
3 bedrooms, 3 beds, 2.5 bathrooms
28 Nov – 3 Dec
4.98 out of 5 average rating, 88 reviews
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Guest favourite
Home in Monroe
Gorgeous 5BR lakefront home, private beach & dock
5 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
4.95 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Goshen
Unique Dutch Barn in the Hudson Valley
5 bedrooms, 9 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 116 reviews