Chester Holiday Rentals

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Holiday Rentals in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AU$386
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Located next to the Ski Resort, Bike Park and Water Park

10.0 out of 10, Exceptional, (153)
"It’s our second time staying in this condo. We love it and hope to use it again. "
Located next to the Ski Resort, Bike Park and Water Park

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

10.0 out of 10, Exceptional, (21)
"The house is absolutely beautiful. My son named it the “Triangle House” Very clean. All supplies were available..towels, linens, etc. Plenty of activities to do in the area. We explored High Point State Park, went zip-lining at TreEscape, dinner in Warwick. Overall a great little getaway!"
Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (28)
"Beautiful property, with cozy linens in every room, incredibly well maintained property, and lovely views. The welcome book had clear instructions, there were great lawn games, lots of suggestions to eat too. The icing on the cake was the welcome basket, complete with Halloween treat bag for our little one! "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.2 out of 10, Wonderful, (15)
"Hikers’ Haven was a beautiful getaway. Vin was a great host and the cabin was cozy and well located"
The price is AU$244
includes taxes & fees
1 Dec - 2 Dec
Cozy Loft Cabin high above Bashakill Wildlife Refuge

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

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AU$546
includes taxes & fees
2 Dec - 3 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (125)
"What a great family trip. Great location. Great home.Views were outstanding. Owner was alway available and willing to help. Would stay here again when we return to the area. "
Lakefront Luxury on Greenwood Lake

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is AU$1,304
includes taxes & fees
26 Nov - 27 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Cabin in the heart of the Hudson Valley, Cabin 4

8.8 out of 10, Excellent, (18)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is AU$254
includes taxes & fees
2 Dec - 3 Dec
Cabin in the heart of the Hudson Valley, Cabin 4

Quaint village, walk to restaurants and shops.

9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.

Cottage Suites

3.0 star property
8.0 out of 10, Very good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites

Catskills cabin over waterfall with views & hot tub

9.8 out of 10, Exceptional, (64)
"We looked forward to a get away to enjoy the Catskills foliage in October and this cabin checked all the boxes. The owners, Adam and Chrissy, were more than helpful in answering our questions (especially the last minute TV questions before a big game, and how to operate the shower). They welcomed our larger old dog, which was priceless. The inside of the cabin is cozy and nostalgic, but you cannot beat the view! We loved listening to the waterfall below, the layers of colors in the foliage were...
Catskills cabin over waterfall with views & hot tub

Entire Lakehouse Cabin by Mountain Creek & Warwick

10.0 out of 10, Exceptional, (107)
"A beautifully decorated cabin in a quaint lakeside neighborhood. Such attention to detail , everything you need is there for a relaxing, comfortable stay. "
Entire Lakehouse Cabin by Mountain Creek & Warwick

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

9.6 out of 10, Exceptional, (21)
"Enjoyed the accommodation and all tge area had to offer. We did the Sky ride and Coaster So Great. Went to Warwick Apple Festival Awesomeness and Blue Arrow Farm for concert. Highly recommend "
The price is AU$508
includes taxes & fees
26 Nov - 27 Nov
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Renovated 1850's Cottage on Storm King Mountain

9.8 out of 10, Exceptional, (14)
"Great place!"
Renovated 1850's Cottage on Storm King Mountain

Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118

9.8 out of 10, Exceptional, (114)
"Lakefront House on Greenwood Lake is awesome. We were in town to visit Watchtower Headquarters in Warwick. The house was clean and comfortable. Communication was Jody was quick. We enjoyed the lake so much! We look forward to returning again."
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (40)
"We loved our two nights here! Space was spotless and comfortable for 4 of us. Location was central to everything. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Luxury Retreat: Near Skiing, Hot Tub, Game Room, Playground! Pool in summer!

10.0 out of 10, Exceptional, (15)
"Our group enjoyed our stay at this property! The host was very responsive, and the house was a great set-up! The location was close enough to town but still serene. Would recommend this property for any group or family to stay. "
Luxury Retreat: Near Skiing, Hot Tub, Game Room, Playground! Pool in summer!
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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Other types of properties in Chester you may be interested in

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

2.5 star property
8.4 out of 10, Very good, (1011)
"Our stay was great But when we checked in we waited a good 15 minutes before someone greeted us at the front desk. "
The price is AU$165
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

DoubleTree by Hilton Hotel Nanuet

4.0 star property
8.6 out of 10, Excellent, (1021)
"The rooms are large and nicely decorated. They are quiet and comfortable. Two small issues - the bathroom sink didn’t drain very well and the desk chair looked like it had been dragged across a rough surface. The upholstery was torn away at the edges. Every thing was very clean."
The price is AU$202
includes taxes & fees
8 Dec - 9 Dec
DoubleTree by Hilton Hotel Nanuet

Super 8 by Wyndham Mahwah

2.5 star property
7.4 out of 10, Good, (1009)
"This hotel was adequate as a no frills hotel. The grab and go was very disappointing. "
The price is AU$132
includes taxes & fees
16 Dec - 17 Dec
Super 8 by Wyndham Mahwah
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.
Beautiful view of the beach with palm trees

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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 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 12 holiday rentals for your stay in Chester.

What can I see and do in Chester?

The Rock Sports Complex and Goosepond Mountain State Park are a couple of scenic spots to enjoy the outdoors, whereas Museum Village is one of the cultural attractions. Castle Fun Center and Woodbury Common Premium Outlets are a couple of places you'll find 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.