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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (7)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AED 951
AED 1,205 total
includes taxes & fees
11 May - 12 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

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!
Fridge, microwave, stovetop, dishwasher

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.
Terrace/patio

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.
Miscellaneous

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

10.0 out of 10, Exceptional, (4)
"Wonderful property with a comfortable, laid back vibe! Highly recommend! However, parking is a bit tight so leave the F-250 Extended Cab home! "
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.
Fridge, microwave, oven, stovetop

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
Outdoor dining

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (40)
"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!
Fridge, microwave, stovetop, dishwasher

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
Outdoor dining

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
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (288)
"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 AED 1,429
AED 1,870 total
includes taxes & fees
12 May - 13 May
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Smart TV, fireplace

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.
Outdoor dining

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 AED 1,175
AED 1,623 total
includes taxes & fees
11 May - 12 May
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.
Greenwood Lake Lakefront Luxury
Property grounds

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (132)
"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
Outdoor spa tub

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

9.8 out of 10, Exceptional, (51)
"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 AED 1,010
AED 1,908 total
includes taxes & fees
13 May - 14 May
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Contemporary Cozy Cottage
Interior

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 AED 918
AED 1,587 total
includes taxes & fees
11 May - 12 May
Contemporary Cozy Cottage
Modern, Magical Woodsy Escape 1 Hour From NYC
Fridge, microwave, oven, stovetop

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
Outdoor dining

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (77)
"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
Fridge, microwave, oven, stovetop

Cozy Rustic Farmhouse With Wood Stove

Cozy Rustic Farmhouse With Wood Stove
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Dining

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
Outdoor pool

Mid-Hudson Estate on 11 acres with pool

10.0 out of 10, Exceptional, (4)
"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
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (7)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AED 951
AED 1,205 total
includes taxes & fees
11 May - 12 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cozy Cabin with Sauna & Firepit!
Outdoor dining

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (25)
"Excellent "
Cozy Cabin with Sauna & Firepit!
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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