Chester Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Chester

Interior
Luxury 9BR Retreat w/Pool & Hot Tub
Luxury 9BR Retreat w/Pool & Hot Tub
Luxury 9BR Retreat w/Pool & Hot Tub
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, (39)
"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 HK$1,112
HK$2,324 total
includes taxes & fees
26 Oct - 27 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is HK$1,462
HK$2,357 total
includes taxes & fees
28 Oct - 29 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (40)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is HK$2,014
HK$2,603 total
includes taxes & fees
1 Nov - 2 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, stovetop, dishwasher
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
8.6 out of 10, Excellent, (88)
"Accommodating host with great communication. We "
The price is HK$1,224
HK$3,251 total
includes taxes & fees
21 Oct - 22 Oct
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (26)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is HK$847
HK$1,368 total
includes taxes & fees
20 Oct - 21 Oct
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is HK$1,773
HK$2,807 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
Property grounds
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
10.0 out of 10, Exceptional, (69)
"We had a great stay."
The price is HK$1,027
HK$2,152 total
includes taxes & fees
19 Oct - 20 Oct
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Terrace/patio
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
10.0 out of 10, Exceptional, (34)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
The price is HK$1,399
HK$3,021 total
includes taxes & fees
2 Nov - 3 Nov
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Dining tables
Chestnut on Willow Lake
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is HK$3,110
HK$4,549 total
includes taxes & fees
30 Oct - 31 Oct
Chestnut on Willow Lake
Outdoor pool, a heated pool
Located next to the Ski Resort, Bike Park and Water Park
Located next to the Ski Resort, Bike Park and Water Park
9.8 out of 10, Exceptional, (170)
"Family lives in Warwick NY & this was the perfect distance from their home! Kristof & Barbara were awesome hosts & their condo was great!!"
Located next to the Ski Resort, Bike Park and Water Park
Children’s area
Hickory on Willow Lake
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 HK$3,304
HK$4,772 total
includes taxes & fees
20 Oct - 21 Oct
Hickory on Willow Lake
Property grounds
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
10.0 out of 10, Exceptional, (52)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is HK$847
HK$2,063 total
includes taxes & fees
21 Oct - 22 Oct
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
Interior
The Perfect Essential Getaway!
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 HK$7,191
HK$9,911 total
includes taxes & fees
19 Oct - 20 Oct
The Perfect Essential Getaway!
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (14)
"Very cozy stay with responsive host"
The price is HK$3,149
HK$5,299 total
includes taxes & fees
19 Oct - 20 Oct
Large,Cozy,Bright Apartment, Business Themed.
Exterior
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Property grounds
The Woodbury Cottage
The Woodbury Cottage
9.0 out of 10, Wonderful, (26)
"A cozy place to stay. "
The Woodbury Cottage
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
10.0 out of 10, Exceptional, (309)
"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
Interior
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries
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
Interior
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
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
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Excellent staff at a beautiful hotel"
Nancy 3-night trip
Posted 1 day ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out: This holiday home rental outside of Chester is located in the mountains, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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.