Chester Holiday Rentals

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Holiday Rentals in Chester

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (24)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is AU$647
includes taxes & fees
28 July - 29 July
Contemporary Cozy Cottage

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is AU$652
includes taxes & fees
29 July - 30 July
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is AU$903
includes taxes & fees
30 July - 31 July
Chestnut on Willow Lake

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 AU$954
includes taxes & fees
29 July - 30 July
Hickory on Willow Lake

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

9.8 out of 10, Exceptional, (26)
"Plenty of room for my family"
The price is AU$548
includes taxes & fees
29 July - 30 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is AU$1,276
includes taxes & fees
29 July - 30 July
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is AU$537
includes taxes & fees
4 Aug - 5 Aug
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is AU$560
includes taxes & fees
4 Aug - 5 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is AU$1,943
includes taxes & fees
14 Aug - 15 Aug
Room for Everyone: Spacious 6BR West Point Retreat

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is AU$1,051
includes taxes & fees
2 Aug - 3 Aug
Large, Cozy, Bright Business Class Corporate Retreat

complete privacy vacation home [private pool]

9.8 out of 10, Exceptional, (8)
"Wonderful property! The pool was so fun!"
The price is AU$1,755
includes taxes & fees
24 July - 25 July
complete privacy vacation home [private pool]

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

10.0 out of 10, Exceptional, (298)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is AU$909
includes taxes & fees
3 Aug - 4 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

5BR Home with Sauna & Pool Hot tub Fire pit

The price is AU$2,363
includes taxes & fees
28 July - 29 July
5BR Home with Sauna & Pool Hot tub Fire pit

Indoor Pool Paradise | 6BR + Huge Decks

The price is AU$3,135
includes taxes & fees
27 July - 28 July
Indoor Pool Paradise | 6BR + Huge Decks

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is AU$1,938
includes taxes & fees
2 Aug - 3 Aug
The Perfect Essential Getaway!

Amazing Home Near West Point, Shopping, Skiing and Legoland

10.0 out of 10, Exceptional, (12)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
The price is AU$728
includes taxes & fees
3 Aug - 4 Aug
Amazing Home Near West Point, Shopping, Skiing and Legoland

New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control.

8.6 out of 10, Excellent, (8)
"Very nice area near plenty of nice things to do and see. Comfortable and clean as well."
The price is AU$782
includes taxes & fees
24 July - 25 July
New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control.

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.6 out of 10, Exceptional, (53)
"Family REALLY loved our stay here. House was gorgeous and roomy. Backyard was amazing, fire pits and well maintained. Kelly, property management, were attentive and very kind. Saving this on favorites for our next trip"
The price is AU$675
includes taxes & fees
30 July - 31 July
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Wake Up to Water Views:Secluded 1 Acre Waterfront Retreat near New Paltz & Gunks

9.6 out of 10, Exceptional, (4)
"My family and I stayed here for the weekend for a family wedding and it was wonderful. The hosts were very responsive, the place was very clean, and the outdoor setting was really beautiful. It was such a relaxing setting. If we're in the area again, we'd definitely stay here. "
The price is AU$953
includes taxes & fees
29 July - 30 July
Wake Up to Water Views:Secluded 1 Acre Waterfront Retreat near New Paltz & Gunks

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AU$979
includes taxes & fees
28 July - 29 July
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Castle Fun Center, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffee shops during your trip.

What are some of the best holiday rentals that Chester has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chester?

Expedia has 11 holiday rentals for your stay in Chester.

What can I see and do in Chester?

Family-friendly attractions include Castle Fun Center, whereas The Rock Sports Complex is a spot to enjoy the outdoors. You’ll find favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.