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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 AED 951
AED 1,084 total
includes taxes & fees
28 Mar - 29 Mar

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, (46)

Red Barn Retreat - Shawangunk Mountains Getaway
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (36)

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

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

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 AED 951
AED 1,084 total
includes taxes & fees
28 Mar - 29 Mar

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 AED 676
AED 955 total
includes taxes & fees
31 Mar - 1 Apr
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

La Quinta Inn & Suites by Wyndham Middletown
5/5 Excellent
Accommodating
"Anthony at the front desk was absolutely AMAZING. He was very kind, understanding and accommodating for us after I explained our situation."
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Middletown
Posted 23 hours ago