Over 1,000 places in Chester

Guest favorite
Guest suite in Chester
Adorable Guest Apartment in Victorian Mansion
2 beds
Apr 7 – 12
4.96 out of 5 average rating, 224 reviews
Guest favorite
Home in Chester
Millionaire Mansion (Hottub, BBQ, Spa, Games, More
8 beds
Apr 7 – 12
5.0 out of 5 average rating, 58 reviews
Guest favorite
Guest suite in Chester
Cozy Suite in Victorian Mansion
1 queen bed
Apr 2 – 7
5.0 out of 5 average rating, 42 reviews
Superhost
Home in Chester
Private Relaxing Secluded Home with heated Pool.
7 beds
Apr 1 – 6
5.0 out of 5 average rating, 30 reviews
Guest favorite
Home in Goshen
Cozy Brookside Cottage on the Farm
2 beds
Aug 4 – 9
4.97 out of 5 average rating, 39 reviews
Guest favorite
Apartment in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 queen beds
Apr 14 – 19
4.96 out of 5 average rating, 330 reviews
Guest favorite
Apartment in Chester
Private Country Getaway
5 beds
Apr 29 – May 4
5.0 out of 5 average rating, 10 reviews
Home in Chester
6 bedroom nice big colonial house
8 beds
Apr 1 – 6
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Greenwood Lake
New Listing * The Lake House on Greenwood Lake, NY
3 beds
Apr 5 – 10
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Chester
Relaxing 5BD Close to Adventures Shops & Exploring
6 beds
Apr 1 – 6
5.0 out of 5 average rating, 9 reviews
Home in Chester
Stone Sanctuary
4 beds
Apr 5 – 10
5.0 out of 5 average rating, 4 reviews
Home in Chester
Spacious Home with Pool
7 beds
Apr 12 – 17
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Chester
The Little Green Farmhouse
5 beds
Apr 1 – 6
4.98 out of 5 average rating, 119 reviews
Guest favorite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
5 beds
Apr 1 – 6
4.94 out of 5 average rating, 17 reviews
Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
20 beds
Apr 2 – 7
4.84 out of 5 average rating, 68 reviews
Guest favorite
Home in Greenwood Lake
Love the great outdoors?Picture yourself here!
5 beds
Apr 21 – 26
5.0 out of 5 average rating, 84 reviews
Guest favorite
Home in Chester
1841 Farmhouse located in the Warwick Valley!
6 beds
Apr 1 – 6
4.96 out of 5 average rating, 68 reviews
Guest favorite
Home in Greenwood Lake
Modern Craftsman Lakeside Retreat
3 king beds
Apr 8 – 13
5.0 out of 5 average rating, 91 reviews