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Search results; Over 1,000 homes in Chester

Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 private bathrooms
13–18 Jul
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4.98 out of 5 average rating, 160 reviews
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 383 reviews
Guest favourite
Guest suite in Chester
Cozy Guest Suite in Historic Victorian Mansion
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.94 out of 5 average rating, 231 reviews
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds, 2.5 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 44 reviews
Guest favourite
Flat in Chester
Rekindled Farmhouse
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
4.92 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chester
“The Loaf” in Sugar Loaf NY
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Jul
4.84 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
4 bedrooms, 5 beds, 3.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 425 reviews
Guest favourite
Villa in Chester
11BR Escape w/ Pool, Hot Tub, Sauna & Game Room
11 bedrooms, 29 beds, 4 bathrooms
20–25 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Woodbury
Maple Ridge Retreats Apt. A
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
5.0 out of 5 average rating, 81 reviews
Guest favourite
Guest house in Chester
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 19 reviews
Superhost
Home in Monroe
NEW Luxury Lakefront Retreat | Pool, Boats & Games
4 bedrooms, 4 beds, 4 bathrooms
12–17 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Warwick
Green Pond Farmhouse Downstairs
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
4 bedrooms, 5 beds, 3.5 bathrooms
5–10 Jul
4.99 out of 5 average rating, 177 reviews
Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
4.89 out of 5 average rating, 400 reviews
Top guest favourite
Cabin in Greenwood Lake
Cabinessence -on Greenwood Lake, NY #34370
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 482 reviews
Guest favourite
Home in Greenwood Lake
Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
3 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 105 reviews
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #3
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Monroe
Studio Lakeside Retreat | Fast WiFi & Great WFH
1 bedroom, 2 single beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 8 reviews