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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
9.6 out of 10, Exceptional, (5)
The price is SAR 972
SAR 1,235 total
includes taxes & fees
8 Apr - 9 Apr

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

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, (17)

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, (2)

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, (37)

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
9.6 out of 10, Exceptional, (5)
The price is SAR 972
SAR 1,235 total
includes taxes & fees
8 Apr - 9 Apr

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (108)
The price is SAR 630
SAR 1,053 total
includes taxes & fees
8 Apr - 9 Apr

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
9.8 out of 10, Exceptional, (57)
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

Thayer Hotel
5/5 Excellent
"What a memorable stay. So clean, so much rich history, and the staff was amazing. Highly recommend. "
A verified traveler stayed at Thayer Hotel
Posted 13 hours ago