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Vacation Homes in Chester

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

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is SAR 972
SAR 1,240 total
includes taxes & fees
31 Aug - 1 Sep
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

10.0 out of 10, Exceptional, (303)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is SAR 1,517
SAR 2,035 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

10.0 out of 10, Exceptional, (3)
"Awesome place. Cozy and great communication with owners. "
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

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

9.4 out of 10, Exceptional, (36)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
The price is SAR 539
SAR 1,150 total
includes taxes & fees
25 Aug - 26 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is SAR 976
SAR 2,178 total
includes taxes & fees
15 Sep - 16 Sep
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The location is close to legoland which is nice. They had connect 4 and some playing cards otherwise the property isnt great for little ones due to some odd decor choices. There were ants and a spider and unsure about the cleaning. Thermostat didnt adjust and dishwasher didnt work. Tvs were hard to use. Wish there had been printed instructions for where to find things in the house, as well as recommendations in the town. Didnt use outdoor deck because too cold but also couldnt open the door and...
Stylish & Peaceful Getaway on 3 Private Acres

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

7.0 out of 10, Good, (2)
"Nice to have top notch bar/restaurant downstairs!"
The price is SAR 405
SAR 662 total
includes taxes & fees
16 Sep - 17 Sep
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (22)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (11)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cozy property with privacy and comfort. "
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

10.0 out of 10, Exceptional, (52)
"This was our third visit with family (6 adults, two children) and again it was a wonderful experience. Pool, hot tub, beautiful property, everything delightful."
Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

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

2.0 star property
9.4 out of 10, Exceptional, (8)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (53)
"The property is close to Minawaska State Park where we went hiking. We enjoyed the hot tub and had a nice stay. There are a number of nice restaurants nearby too."
Red Barn Retreat - Shawangunk Mountains Getaway

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

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!

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

9.6 out of 10, Exceptional, (11)
"We loved the new furniture and sheets and blankets. Everything was spotless and felt super comfortable and homey. Big space as well! "
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Large,Cozy,Bright Apartment, Business Themed.

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is SAR 1,520
SAR 2,474 total
includes taxes & fees
23 Aug - 24 Aug
Large,Cozy,Bright Apartment, Business Themed.

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (34)
"We had a peaceful stay here while we were in town for a few days.The cabin was very cute, clean, and the neighborhood/ neighbors were very quiet. The steps into the bathroom and bedroom were illuminated and the upstairs loft was a cool getaway for our teenager.Recommend taking a bigger vehicle that can take a rough gravel road."
Cozy Cabin with Sauna & Firepit!

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

8.0 out of 10, Very Good, (1)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
The price is SAR 1,032
SAR 1,853 total
includes taxes & fees
24 Aug - 25 Aug
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

8.8 out of 10, Excellent, (6)
"I stayed here for the weekend to hike a small section of the AT. It was perfect for my trip. "
The price is SAR 287
SAR 558 total
includes taxes & fees
24 Aug - 25 Aug
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
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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Top Chester Hotel Reviews