Search results; 368 places in Chester

Prices include all fees
Superhost
Villa in Chester
Mansion, Heated Pool, HotTub, FirePit, Huge B'yard
20 beds
Jun 16 – 21
R124,365 ZAR for 5 nights, originally R152,514 ZAR
for 5 nights
4.86 out of 5 average rating, 111 reviews
Guest favorite
Cottage in Monroe
Cozy Lake Cabin
3 beds
Jun 11 – 16
R37,667 ZAR for 5 nights, originally R58,646 ZAR
for 5 nights
4.99 out of 5 average rating, 158 reviews
Superhost
Home in Monroe
Winter Home near Legoland, West Point & Outlet
3 beds
Jun 15 – 20
R25,778 ZAR for 5 nights, originally R37,728 ZAR
for 5 nights
4.86 out of 5 average rating, 146 reviews
Top guest favorite
Cottage in Warwick
Ranch in the Woods | A Peaceful Designer Retreat
Free cancellation
Jun 27 – Jul 2
R37,772 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 58 reviews
Chalet in Port Jervis
One of a kind A-Frame-Movies~Arcade~HTub~60-mi~NYC
7 beds
Jun 22 – 27
R48,868 ZAR for 5 nights, originally R52,846 ZAR
for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Room in Nyack
Stay with JaimeConstruction,
Cul-de-sac 1-bedroom, includes free parking!
Jun 11 – 16
R6,250 ZAR for 5 nights, originally R6,834 ZAR
for 5 nights
4.88 out of 5 average rating, 73 reviews
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Guest favorite
Cabin in Warwick
Magnificent Log Cabin Getaway with Private Lake
5 beds
Jun 12 – 17
R46,126 ZAR for 5 nights, originally R60,059 ZAR
for 5 nights
4.97 out of 5 average rating, 120 reviews
Top guest favorite
Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
5 beds
Jul 9 – 14
R123,478 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 116 reviews
Home in Goshen
Near Lego Land 5-brm home with free parking+wifi
6 beds
Jun 13 – 18
R47,872 ZAR for 5 nights
for 5 nights
4.58 out of 5 average rating, 53 reviews
Room in Fishkill
Stay with JessicaRegional manager,
Charming Private Room with Pool Access
Jul 13 – 18
R7,207 ZAR for 5 nights
for 5 nights
New place to stay
Superhost
Vacation home in Woodbury
Malkita’s Mountain View Villa
10 beds
Jun 15 – 20
R75,754 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 82 reviews
Guest favorite
Home in Warwick
Summer Retreat! Amazing Pool, Playground, 7 acres!
Free cancellation
Jun 22 – 27
R66,959 ZAR for 5 nights, originally R112,848 ZAR
for 5 nights
4.93 out of 5 average rating, 108 reviews
Superhost
Home in Bloomingburg
Δ Scenic Hiking Paradise with Deck and Fire Pit!
5 beds
Jun 13 – 18
R13,425 ZAR for 5 nights, originally R17,001 ZAR
for 5 nights
4.8 out of 5 average rating, 551 reviews
Guest favorite
Tiny home in Ellenville
No Cleaning Fee - Tiny Home, King Bed & Hot Tub
Free cancellation
Jul 13 – 18
R16,215 ZAR for 5 nights, originally R25,309 ZAR
for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Place to stay in New Hampton
Luxury School House W/ Sauna/Pool - 1 HR from NYC
5 beds
Jun 22 – 27
R101,848 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 42 reviews
Home in Wurtsboro
Bashakill House
3 beds
Jun 11 – 16
R25,777 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Condo in Vernon Township
Appalachian Lodge Top Floor w/views
2 beds
Jun 22 – 27
R14,588 ZAR for 5 nights, originally R15,903 ZAR
for 5 nights
4.94 out of 5 average rating, 846 reviews
Top guest favorite
Cabin in Cuddebackville
Sauna & Hot Tub Creekfront Oasis · Hikers Hollow
4 beds
Jul 6 – 11
R30,196 ZAR for 5 nights, originally R35,684 ZAR
for 5 nights
4.98 out of 5 average rating, 132 reviews