Chester Holiday Rentals

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Holiday Rentals in Chester

Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY

10.0 out of 10, Exceptional, (3)
"The farmhouse is clean, comfortable, has modern updates to a rustic house. The owner/host was very pleasant and unobtrusive. We would definitely stay here again."
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is AU$466
includes taxes & fees
29 July - 30 July
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

10.0 out of 10, Exceptional, (299)
"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$902
includes taxes & fees
3 Aug - 4 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

10.0 out of 10, Exceptional, (43)
"Great Location and responsive owner. Thank you"
The price is AU$412
includes taxes & fees
3 Aug - 4 Aug
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (62)
"Beautiful views!"
The price is AU$483
includes taxes & fees
27 July - 28 July
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

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$974
includes taxes & fees
28 July - 29 July
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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$544
includes taxes & fees
29 July - 30 July
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, (7)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is AU$238
includes taxes & fees
29 July - 30 July
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (1)
"Highly recommended! Such a vibe, quiet & cozy. You can hear the birds in the morning, so peaceful. I would go back!! "
The price is AU$296
includes taxes & fees
29 July - 30 July
Romantic spot above restaurant., ideal for the gourmet

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

9.4 out of 10, Exceptional, (32)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
The price is AU$468
includes taxes & fees
28 July - 29 July
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

9.0 out of 10, Wonderful, (4)
"I stayed here for the weekend to hike a small section of the AT. It was perfect for my trip. "
The price is AU$228
includes taxes & fees
29 July - 30 July
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

Indoor Pool Paradise | 6BR + Huge Decks

Indoor Pool Paradise | 6BR + Huge Decks

Condo at Mtn Creek 2 Bdr 2 Bath sleep 8 Mtn view #212

10.0 out of 10, Exceptional, (4)
"What an enjoyable experience. So easy to book and answered every question so quickly. Beautiful property. All communication was so detailed and made the whole rental process easy.Enjoyed our stay. Thanks Millie and Sergio!"
The price is AU$823
includes taxes & fees
29 July - 30 July
Condo at Mtn Creek 2 Bdr 2 Bath sleep 8 Mtn view #212

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

9.8 out of 10, Exceptional, (82)
"Amazing property for a large get together of family and friends! Kitchen is well stocked. Legos and games to keep children entertained! House was clean and had plenty of space. We came to ski but would consider coming back for other seasons as well "
The price is AU$3,229
includes taxes & fees
10 Aug - 11 Aug
Luxurious/Private-Heated pool, Hot tub & Tennis/Golf/Ski in-Ski Out Mnt. Creek

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.6 out of 10, Excellent, (4)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is AU$216
includes taxes & fees
29 July - 30 July
The Warwick Inn Boutique Amity Room 3 an Hour from NYC

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

8.8 out of 10, Excellent, (80)
"Wish we could have stayed longer. Great place and lots of room for your whole family. "
The price is AU$651
includes taxes & fees
28 July - 29 July
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at the Appalachian Resort hosted by Milagros & Sergio. They were incredibly friendly and gave us clear and helpful explanations from the start. The room was very clean, and it was great having the water park within walking distance. They also offered flexible early check-in depending on the situation, which we really appreciated. Whenever we had questions, they responded very quickly, so we felt completely comfortable during our stay. We would love to come back again!"
The price is AU$411
includes taxes & fees
28 July - 29 July
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (28)
"Very nice cabin that is nicely keep with everything you need. I will be hoping to visit again "
The price is AU$626
includes taxes & fees
31 July - 1 Aug
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Vernon Condo w/ Deck, Near Appalachian Trail!

7.8 out of 10, Good, (38)
"The place was absolutely beautiful. Want to come back again very soon"
Vernon Condo w/ Deck, Near Appalachian Trail!
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.