Holiday Homes in Chester

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Featured Holiday Homes in Chester

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

9.8 out of 10, Exceptional, (15)
"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

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AU$801
includes taxes & fees
21 Oct - 22 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is AU$548
includes taxes & fees
27 Oct - 28 Oct
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, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is AU$1,047
includes taxes & fees
12 Oct - 13 Oct
Large,Cozy,Bright Apartment, Business Themed.

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

9.4 out of 10, Exceptional, (38)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
The price is AU$468
includes taxes & fees
7 Oct - 8 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Hickory on Willow Lake

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AU$937
includes taxes & fees
2 Oct - 3 Oct
Hickory on Willow Lake

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

9.4 out of 10, Exceptional, (39)
"Very nice location and spacious house.Bbq grill could be better"
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

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

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

10.0 out of 10, Exceptional, (22)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Spacious 6BR Villa - Serene Scenic Mountain Escape

10.0 out of 10, Exceptional, (4)
"The house was fantastic as was the host. Our group had an amazing weekend together and I highly recommend"
Spacious 6BR Villa - Serene Scenic Mountain Escape

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

10.0 out of 10, Exceptional, (56)
"This property is STUNNING and the hosts are just lovely! The on-site amenities, nearby wineries, Angry Orchard Cider House, Gardiner (Wilflower Farms restaurant is to die for), New Paltz farmers market, and Gunks hiking are all incredible. Cannot recommend a stay here enough! "
Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

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

9.8 out of 10, Exceptional, (86)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (35)
"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!

The Woodbury Cottage

8.8 out of 10, Excellent, (25)
"A cozy place to stay. "
The Woodbury Cottage

Harriman Outdoor Center - White Oak Cabin

The price is AU$400
includes taxes & fees
5 Oct - 6 Oct
Harriman Outdoor Center - White Oak Cabin

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

10.0 out of 10, Exceptional, (39)
"Everything was good. Heather was very attentive."
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Red Cabin Lake House with Amazing Views!

2.0 out of 10, (1)
"Fishing/Lake: There is absolutely no access to the lake, including the community beach. No swimming. No fishing. Such details must be in the property's details in caps. Fishing or swimming is not allowed. Water: Smelly brown water in the house. You can’t drink it or cook with it or even take a shower. It is disguising. No heads-up about the water issue. Kitchen: The smell of dirty dishes welcomed us. It looks like the previous renters left them there. Only 4 forks and 1 knife in the house....
Red Cabin Lake House with Amazing Views!

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (142)
"We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!"
Greenwood Lake Lakefront Luxury
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
866
Accommodation
374 Holiday Homes
Lowest Price
AU$400
Highest Price
AU$1,047

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