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Compare 286 Vacation Homes in Chester with updated reviews, rates, and availability.

Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (32)
"We had a great time staying in Gardiner, NY. The Red Barn Retreat was perfect! There are so many things to do near this location. We visited Hyde Park, had lunch at the Culinary Institute, hiked the Monhonk Preserve, explored Historic Huguenot Street, checked out New Paltz for the first time and did the Walkway Over the Hudson on the way home. I loved relaxing under the stars in the hot tub and just gazing out at the view. My spouse just asked me last night, "When are we going back?" Bill is a...
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
9.6 out of 10, Exceptional, (4)
"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."
The price is SAR 2,684
SAR 4,158 total
includes taxes & fees
16 Dec - 17 Dec
complete privacy vacation home [private pool]
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is SAR 1,518
SAR 3,145 total
includes taxes & fees
25 Nov - 26 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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 642
SAR 1,329 total
includes taxes & fees
3 Dec - 4 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (22)
"House was beautifully furnished with lovely touches of art work and lovely succulent plants. The hot tub was a great touch, and we enjoyed it every morning. The children loved exploring the property. Thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Nature Getaway: Charming Villa Near Trails and Parks
7.2 out of 10, Good, (9)
"Really cool house. We has some issues with our stay. It took a bit to get in touch with the manager to resolve the issues. The next day the brought most if the items needed that the h"
Nature Getaway: Charming Villa Near Trails and Parks
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!
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
8.0 out of 10, Very Good, (5)
"The home was in a perfect spot with lake views and is nicely close to town. We picked the home for its closeness to the rein fair and I’m so glad we did, It was wonderfully quiet and relaxing after a long day of hanging out at the rein fair !"
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
Perfect for families and large groups
9.4 out of 10, Exceptional, (10)
"Nice house with plenty of room and very clean."
Perfect for families and large groups
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
9.8 out of 10, Exceptional, (114)
"Lakefront House on Greenwood Lake is awesome. We were in town to visit Watchtower Headquarters in Warwick. The house was clean and comfortable. Communication was Jody was quick. We enjoyed the lake so much! We look forward to returning again."
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (14)
"Secluded and filled with every conveniece you might desire. We especially appreciated the air fryer for our leftovers!"
The price is SAR 939
SAR 1,415 total
includes taxes & fees
24 Nov - 25 Nov
Contemporary Cozy Cottage
5 Acre Modern Mountain Farm
9.4 out of 10, Exceptional, (28)
"We enjoyed our stay. The property is beautiful. Some extra bath towels would be nice. We would definitely stay again!"
The price is SAR 1,029
SAR 1,934 total
includes taxes & fees
9 Dec - 10 Dec
5 Acre Modern Mountain Farm
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (23)
"The home was very clean and had everything we needed - snacks games and a cute patio. The internet was iffy and never worked to stream on the bedroom tv. They came and checked it , but it didn’t improve. The host was very responsive and offered to ship an item our daughter left. We would rent again. "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Private Mountain Creek Getaway!
8.0 out of 10, Very Good, (4)
"We enjoyed our stay. The place had all we needed. It was super close to Mountain Creek - Our last adventure for our daughters who had raced together for 6 years amd are now off to college!!! All communications were clear and Charlie responded quickly with any questions."
The price is SAR 967
SAR 1,964 total
includes taxes & fees
24 Nov - 25 Nov
Private Mountain Creek Getaway!
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, (18)
"Loved the layout and the amount of natural light"
Sweet and spacious mountain view home w/fireplace!
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 Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
10.0 out of 10, Exceptional, (5)
"No Iocation. Some furniture could use some updating."
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
10.0 out of 10, Exceptional, (18)
"Very homey feeling, close to where we needed to go. Easy on and off from highway."
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Amazing 3BR/3BA! Croton on Hudson!
7.0 out of 10, Good, (2)
"We found the house pleasant and centrally located"
Amazing 3BR/3BA! Croton on Hudson!
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
9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Located next to the Ski Resort, Bike Park and Water Park
10.0 out of 10, Exceptional, (153)
"It’s our second time staying in this condo. We love it and hope to use it again. "
Located next to the Ski Resort, Bike Park and Water Park
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
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.