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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

9.8 out of 10, Exceptional, (6)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is SAR 972
SAR 1,248 total
includes taxes & fees
29 Apr - 30 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

10.0 out of 10, Exceptional, (1)
"Place is absolutely gorgeous, owners are in contact the entire time with very little wait in between messages. I recommended 10/10"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (34)
"Cozy property with great amenities and a perfect location for decompressing after visiting family. we will stay here again!"
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (19)
"Had a great time with friends for a peaceful weekend away from NYC. We loved the house and it was just what we needed!"
Catskills mountain gateway house.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (3)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (48)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (38)
"My son and I stayed here for 2 nights and it was perfect for nearby hiking, dining and shopping/walking around New Paltz. The hosts were very accommodating and had great recommendations for everything local. My only complaint is not being able to stay longer, we plan to return!"
Red Barn Retreat - Shawangunk Mountains Getaway

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (14)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!

Spacious Westtown Home, Firepit, Up to 10 Guest

10.0 out of 10, Exceptional, (4)
"I stayed for business and this was perfectly located for what I needed to get done in the area. "
Spacious Westtown Home, Firepit, Up to 10 Guest

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (287)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is SAR 1,459
SAR 1,945 total
includes taxes & fees
29 Apr - 30 Apr
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

2.0 star property
9.4 out of 10, Exceptional, (3)
"This home was newly renovated and very clean. Would stay there again."
The price is SAR 1,200
SAR 1,692 total
includes taxes & fees
29 Apr - 30 Apr
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (130)
"What a great family trip. Great location. Great home.Views were outstanding. Owner was alway available and willing to help. Would stay here again when we return to the area. "
Greenwood Lake Lakefront Luxury

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

9.8 out of 10, Exceptional, (50)
"Our family had a truly wonderful winter holiday stay - our kids (3 and 5) loved having the books and toys available to use. The location was super convenient to hiking, snow tubing and indoor playareas. House was clean and the beds were very comfortable - we slept great especially after using the hot tub!"
The price is SAR 1,032
SAR 1,990 total
includes taxes & fees
29 Apr - 30 Apr
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (18)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is SAR 938
SAR 1,529 total
includes taxes & fees
4 May - 5 May
Contemporary Cozy Cottage

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (24)
"great place beautiful setting. The house looks nicer than what is actually in the listing. Comfortable place, very clean, had everything we needed. "
Modern, Magical Woodsy Escape 1 Hour From NYC

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (76)
"Enjoyed thanksgiving at this wonderful home! Nestled in the Catskills it was the perfect, cozy, holiday getaway."
Modern Farmhouse on pristine private 12 Acres

Cozy Rustic Farmhouse With Wood Stove

Cozy Rustic Farmhouse With Wood Stove

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"We loved our stay. Spacious, clean and quiet. Close drive to the Minnewaska State Park, wineries and some local restaurants. Highly recommend for a weekend getaway."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Mid-Hudson Estate on 11 acres with pool

10.0 out of 10, Exceptional, (3)
"Great home that accommodated my family for the weekend. Highly recommend"
Mid-Hudson Estate on 11 acres with pool
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

9.8 out of 10, Exceptional, (6)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is SAR 972
SAR 1,248 total
includes taxes & fees
29 Apr - 30 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"Great place and host!"
The price is SAR 630
SAR 1,040 total
includes taxes & fees
29 Apr - 30 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (24)
"Excellent "
Cozy Cabin with Sauna & Firepit!
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.