Search Vacation Homes in Chester
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Our top choices for Chester vacation homes

Vacation Home in Warwick
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town9.2 out of 10, Wonderful, (7)
$131 nightly
The price is $148
Dec 11 - Dec 12
Total with taxes and fees

Vacation Home in Highland Falls
Sleek Escape: Modern 3 BR- 4 Min from West Point !10.0 out of 10, Exceptional, (2)
$405 nightly
The price is $411
Dec 11 - Dec 12
Total with taxes and fees

Vacation Home in Wurtsboro
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Vacation Home in Warwick
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!10.0 out of 10, Exceptional, (5)
$328 nightly
The price is $371
Dec 14 - Dec 15
Total with taxes and fees

Vacation Home in Highland Falls
House on the Babbling Brook- Quiet 2BR + King Bed!10.0 out of 10, Exceptional, (5)
$393 nightly
The price is $418
Dec 21 - Dec 22
Total with taxes and fees

Vacation Home in Wantage
Lux Lake Neepaulin Front Home7.4 out of 10, Good, (3)
$201 nightly
The price is $217
Dec 14 - Dec 15
Total with taxes and fees

Vacation Home in Goshen
Renovated House w/Hot Tub, Deck, Grill & Fire Pit10.0 out of 10, Exceptional, (58)
$473 nightly
The price is $494
Jan 4 - Jan 5, 2026
Total with taxes and fees

Vacation Home in Highland Falls
Lovely 3BR Home with parking-Walk to WP Gate!10.0 out of 10, Exceptional, (7)
$263 nightly
The price is $295
Dec 22 - Dec 23
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG
10/10 Excellent
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 345 |
|---|---|
Accommodation | 326 Vacation Homes |
Lowest Price | $148 |
Highest Price | $524 |
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