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chester orange county ny
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Over 1,000 places in Chester
Guest favorite
Guest favorite
Guest suite in Chester
Adorable Guest Apartment in Victorian Mansion
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$93
night
$93 per night
4.96 out of 5 average rating, 224 reviews
4.96 (224)
Guest favorite
Guest favorite
Home in Chester
Millionaire Mansion (Hottub, BBQ, Spa, Games, More
8 beds
8 beds
Apr 7 – 12
Apr 7 – 12
$378
$302
night
$302 per night, originally $378
5.0 out of 5 average rating, 58 reviews
5.0 (58)
Guest favorite
Guest favorite
Guest suite in Chester
Cozy Suite in Victorian Mansion
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
$73
night
$73 per night
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Superhost
Superhost
Home in Chester
Private Relaxing Secluded Home with heated Pool.
7 beds
7 beds
Apr 1 – 6
Apr 1 – 6
$379
$231
night
$231 per night, originally $379
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favorite
Guest favorite
Home in Goshen
Cozy Brookside Cottage on the Farm
2 beds
2 beds
Aug 4 – 9
Aug 4 – 9
$103
night
$103 per night
4.97 out of 5 average rating, 39 reviews
4.97 (39)
Guest favorite
Guest favorite
Apartment in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 queen beds
2 queen beds
Apr 14 – 19
Apr 14 – 19
$140
night
$140 per night
4.96 out of 5 average rating, 330 reviews
4.96 (330)
Guest favorite
Guest favorite
Apartment in Chester
Private Country Getaway
5 beds
5 beds
Apr 29 – May 4
Apr 29 – May 4
$120
night
$120 per night
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Home in Chester
6 bedroom nice big colonial house
8 beds
8 beds
Apr 1 – 6
Apr 1 – 6
$369
night
$369 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Greenwood Lake
New Listing * The Lake House on Greenwood Lake, NY
3 beds
3 beds
Apr 5 – 10
Apr 5 – 10
$456
$339
night
$339 per night, originally $456
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favorite
Guest favorite
Home in Chester
Relaxing 5BD Close to Adventures Shops & Exploring
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
$359
night
$359 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Home in Chester
Stone Sanctuary
4 beds
4 beds
Apr 5 – 10
Apr 5 – 10
$171
night
$171 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Home in Chester
Spacious Home with Pool
7 beds
7 beds
Apr 12 – 17
Apr 12 – 17
$306
night
$306 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Chester
The Little Green Farmhouse
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$365
night
$365 per night
4.98 out of 5 average rating, 119 reviews
4.98 (119)
Guest favorite
Guest favorite
Home in Chester
Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$446
night
$446 per night
4.94 out of 5 average rating, 17 reviews
4.94 (17)
Superhost
Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
20 beds
20 beds
Apr 2 – 7
Apr 2 – 7
$1,540
$1,278
night
$1,278 per night, originally $1,540
4.84 out of 5 average rating, 68 reviews
4.84 (68)
Guest favorite
Guest favorite
Home in Greenwood Lake
Love the great outdoors?Picture yourself here!
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
$341
night
$341 per night
5.0 out of 5 average rating, 84 reviews
5.0 (84)
Guest favorite
Guest favorite
Home in Chester
1841 Farmhouse located in the Warwick Valley!
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
$462
night
$462 per night
4.96 out of 5 average rating, 68 reviews
4.96 (68)
Guest favorite
Guest favorite
Home in Greenwood Lake
Modern Craftsman Lakeside Retreat
3 king beds
3 king beds
Apr 8 – 13
Apr 8 – 13
$520
night
$520 per night
5.0 out of 5 average rating, 91 reviews
5.0 (91)
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