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Compare 302 Vacation Homes in Chester with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (42)
"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.
The Perfect up to date Private Getaway to call home for a while
Interior

The Perfect up to date Private Getaway to call home for a while

8.6 out of 10, Excellent, (4)
"This property and listing was perfect for our men's retreat weekend getaway. We gathered together and enjoyed being able to spread out in the spacious home. It was very close to a local park with a pool, basketball court, and open field. We also enjoyed grilling on the patio and using the fire-pit to roast s'mores in the evening. The driveway had plenty of parking. The pool on the property was unusable but the backyard was perfect for us to play football and have outdoor activities. We...
The Perfect up to date Private Getaway to call home for a while
Greenwoods of Warwick
Exterior

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick
Elegant and spacious home with sauna and heated pool
Living area

Elegant and spacious home with sauna and heated pool

Elegant and spacious home with sauna and heated pool
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Living room

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.6 out of 10, Exceptional, (22)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is SAR 599
SAR 1,227 total
includes taxes & fees
6 Jan - 7 January 2025
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Eating area leading to one pristeen acre looking out to waterfront

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is SAR 597
SAR 1,272 total
includes taxes & fees
12 Jan - 13 January 2025
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Exterior

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (30)
"Everything was good and we all enjoyed our stay"
The price is SAR 1,112
SAR 2,028 total
includes taxes & fees
28 Jan - 29 January 2025
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Spectacular ~10k sqft Mansion w/Pool&Tennis
House Exterior

Spectacular ~10k sqft Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (4)
"this house was AMAZING and met every one of our needs and exceeded our expectations. we had 3 children and 19 adults and every person was comfortable. the kids area was perfect and we barely saw them. we already started talking about what we can do next to to have an excuse to stay in the houee again. "
Spectacular ~10k sqft Mansion w/Pool&Tennis
By Mtn Creek Resort: ‘The Point on Highland Lake’
Highland Lakes Vacation Rental | 4BR | 2.5BA | 1,700 Sq Ft | Stairs Required

By Mtn Creek Resort: ‘The Point on Highland Lake’

9.8 out of 10, Exceptional, (60)
"The Point was an excellent choice for our family, plenty of room and things to do for everyone. Please was very well equipped and very clean. The lake area and surrounding area was a great location for us. Highly recommended."
By Mtn Creek Resort: ‘The Point on Highland Lake’
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft

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

9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi
Room

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi
Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.
Exterior

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Exterior

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

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

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (12)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
The price is SAR 2,839
SAR 4,718 total
includes taxes & fees
31 Jan - 1 February 2025
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Delightful Home w/ Fire Pit, Walk to Lake!
Highland Lakes Vacation Rental | 2BR | 1BA | 6 Stairs to Access | 800 Sq Ft

Delightful Home w/ Fire Pit, Walk to Lake!

9.8 out of 10, Exceptional, (9)
"This was a cute house in a beautiful spot of NY. It was cozy and well taken care off. The neighborhood was quiet and beautiful also. We would come agian. "
Delightful Home w/ Fire Pit, Walk to Lake!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson Vacation Rental | 3BR | 2BA | Stairs Required to Access

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (10)
"First time using Vrbo, and I was not disappointed! This property was comfortable, clean and well equipped. We were all very satisfied. "
Bright Cornwall-On-Hudson Vacation Rental!
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
Living area

West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!

10.0 out of 10, Exceptional, (7)
"Everything was great"
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
The Woodbury Cottage
Room

The Woodbury Cottage

9.0 out of 10, Wonderful, (17)
"Great little cottage, nice neighborhood and close to everything "
The Woodbury Cottage
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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is SAR 631
SAR 924 total
includes taxes & fees
6 Jan - 7 January 2025
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Exterior

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (12)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
The price is SAR 2,839
SAR 4,718 total
includes taxes & fees
31 Jan - 1 February 2025
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Home Sweet Home ...

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
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.