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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 ¥38,086
¥48,741 total
includes taxes & fees
Sep 21 - Sep 22
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, (305)
"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!"
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, (6)
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)
"Nice and clean"
The price is ¥21,043
¥43,956 total
includes taxes & fees
Sep 12 - Sep 13
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, (19)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ¥33,116
¥80,086 total
includes taxes & fees
Sep 15 - Sep 16
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 steps upstairs were worrisome, if you have any knee issues - this may not be the best option for a VRBO.This home was super clean, and beautiful however. Plenty of parking space for your guest.All supplies were provided."
The price is ¥42,350
¥63,231 total
includes taxes & fees
Sep 3 - Sep 4
Stylish & Peaceful Getaway on 3 Private Acres

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

8.0 out of 10, Very Good, (3)
"Nice to have top notch bar/restaurant downstairs!"
The price is ¥14,558
¥24,454 total
includes taxes & fees
Sep 3 - Sep 4
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, (12)
"The place was wonderful! Even before check-in, Don was very communicative and made sure to ask about our preferences for one of the rooms.We had a fantastic stay — the home was very spacious, and the layout was perfect for a large family.The highlight for us was the beautiful lake view. We loved the outdoor seating area right by the water — perfect for relaxing with a coffee in the morning or unwinding in the evening. The kayaks were a great bonus and made for some fun time on the lake.We will...
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, (3)
"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, (54)
"Irena and Richard were phenomenal hosts. They were eager help us in any way necessary to ensure an enjoyable stay. We were in the area for my son's graduation from Marist University and the extra days enjoying family times in such a beautiful environment was amazing!"
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, (10)
"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, (55)
"Was a great place to stay and extremely pet friendly! "
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, (10)
"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.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is ¥59,555
¥100,226 total
includes taxes & fees
Sep 3 - Sep 4
Large,Cozy,Bright Apartment, Business Themed.

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

9.2 out of 10, Wonderful, (10)
"We were visiting with friends from the UK and we had a very comfortable stay. Everything we needed, very clean, easy to find and very quiet neighborhood. Would highly recommend."
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

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 ¥11,249
¥21,876 total
includes taxes & fees
Sep 3 - Sep 4
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

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!
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

Find out more about Chester

Find out more about Chester

Chester Vacation Homes information

Number of reviews
Accommodation
374 Vacation Homes
Lowest Price
¥11,249
Highest Price
¥59,555