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Compare 377 Vacation Homes in Chester with updated reviews, rates, and availability.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.8 out of 10, Exceptional, (7)
The price is AED 951
AED 1,205 total
includes taxes & fees
11 May - 12 May

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
10.0 out of 10, Exceptional, (1)

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (34)

Catskills mountain gateway house.
Catskills mountain gateway house.
9.8 out of 10, Exceptional, (19)

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
10.0 out of 10, Exceptional, (4)

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (48)

Red Barn Retreat - Shawangunk Mountains Getaway
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (40)

Bright Cornwall-On-Hudson Vacation Rental!
Bright Cornwall-On-Hudson Vacation Rental!
9.8 out of 10, Exceptional, (14)
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.
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Other property types in Chester

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.8 out of 10, Exceptional, (7)
The price is AED 951
AED 1,205 total
includes taxes & fees
11 May - 12 May

Cozy Cabin with Sauna & Firepit!
Cozy Cabin with Sauna & Firepit!
9.6 out of 10, Exceptional, (25)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
10.0 out of 10, Exceptional, (288)
The price is AED 1,429
AED 1,870 total
includes taxes & fees
12 May - 13 May
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.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

Sleep Inn & Suites Monroe - Woodbury
5/5 Excellent
"Very clean and comfortable!"
A verified traveler stayed at Sleep Inn & Suites Monroe - Woodbury
Posted 2 days ago