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Browse Select Chester Holiday Homes

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

9.8 out of 10, Exceptional, (31)
"Great place for a quiet stay"
The price is £251
includes taxes & fees
21 Sept - 22 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

9.8 out of 10, Exceptional, (13)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

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.

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

9.2 out of 10, Wonderful, (10)
"We loved the house. Our dog accidentally broke part of one of the doors in the home and the host was very understanding! Thanks for a wonderful stay!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

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

10.0 out of 10, Exceptional, (307)
"Perfect place to enjoy family and rest. Open floor plan and scenic lake made it so enjoyable for us. Don is a great communicator with easy check in and check out. A"
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (20)
"Had a wonderful time at the lake. Beautiful, quiet, and calming. "
The price is £400
includes taxes & fees
15 Sept - 16 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (23)
"Great Town with so many adventures. This house is a perfect base of operations for a weekend getaway. Close to restaurants. Great kitchen fun living rooms Comfortable beds. Clean and ready for comfort and fun."
Bright Cornwall-On-Hudson Vacation Rental!

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,

Spacious 6BR Villa - Serene Scenic Mountain Escape

10.0 out of 10, Exceptional, (4)
"We had a great stay. The home was very clean and family friendly. The host was quick to respond to questions and give recommendations Perfect for a Fall weekend! "
Spacious 6BR Villa - Serene Scenic Mountain Escape

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is £490
includes taxes & fees
9 Sept - 10 Sept
Large,Cozy,Bright Apartment, Business Themed.

Luxurious/Private-Heated pool, Hot tub & Tennis/Golf/Ski in-Ski Out Mnt. Creek

9.8 out of 10, Exceptional, (84)
"We Celebrated my sisters 60th birthday. The weekend was filled with LOVE laughter great food great weather and the most amazing accommodations A must see/stay VRBO property. "
Luxurious/Private-Heated pool, Hot tub & Tennis/Golf/Ski in-Ski Out Mnt. Creek

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is £461
includes taxes & fees
9 Sept - 10 Sept
Hickory on Willow Lake

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (10)
"The owner was extremely responsive and the home was very clean."
The price is £272
includes taxes & fees
9 Sept - 10 Sept
Stylish & Peaceful Getaway on 3 Private Acres

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

9.4 out of 10, Exceptional, (39)
"We had a great time! very thoughtful host! would definitely recommend :)"
The price is £343
includes taxes & fees
10 Sept - 11 Sept
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

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 £125
includes taxes & fees
14 Sept - 15 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

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 £365
includes taxes & fees
9 Sept - 10 Sept
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

4 Mi to Hudson River: Cozy Newburgh Home!

9.2 out of 10, Wonderful, (5)
"Great place to stay in Newburgh- house was equipped with everything we needed for a very wonderful 5 days!"
4 Mi to Hudson River: Cozy Newburgh Home!

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (22)
"Great location for a visit to West Point"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Family Friendly Fun + Easy Walk to Main Street Center

9.6 out of 10, Exceptional, (14)
"Responses to our questions was very quick, and everything was handled promptly. Excellent house, very spacious, and quiet neighborhood. Perfect location to visit shops and restaurants. The house was clean and comfortable for the five of us. It was a great week! "
Family Friendly Fun + Easy Walk to Main Street Center
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 Holiday Homes information

Number of reviews
Accommodation
374 Holiday Homes
Lowest Price
£125
Highest Price
£490