Holiday Rentals in Chester

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Holiday Rentals in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is €246
includes taxes & fees
29 Dec - 30 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (12)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
The price is €1,239
includes taxes & fees
3 Jan - 4 Jan 2025
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

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

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (126)
"We needed a place to stay while visiting family in north jersey. This house was perfect - beautiful views, fairly close and clean. Now that we know it is here, we will stay again, God willing. "
Lakefront Luxury on Greenwood Lake

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

10.0 out of 10, Exceptional, (52)
"The view was so good I never turned the TV on once during my stay! I was in town for a wedding and having such a clean, comfy, convenient, and well-apportioned accommodation only added to the joy of the occasion. This is an add-on to the host's residence and it was a comfort to know they were nearby while I was able to enjoy my complete privacy. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

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 €319
includes taxes & fees
14 Jan - 15 Jan 2025
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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

10.0 out of 10, Exceptional, (24)
"The house is beautiful and very clean. Fun game room. Excellent view of the lake. Many sitting areas to enjoy. They provide games and books as well. The owner Neil answered all our questions promptly. Local food leaves a lot to be desired. Definitely AVOID Sussex Sit n Chat diner and avoid Silvio’s Villa (food was severely overpriced and tasted like prison cafeteria food. ) "
Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

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

10.0 out of 10, Exceptional, (42)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

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 €334
includes taxes & fees
12 Jan - 13 Jan 2025
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

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

10.0 out of 10, Exceptional, (154)
"We loved staying here. It’s very clean. It’s right at the base of the slopes! Loved being able to cook breakfast there. The heated outdooor pool was a great unique experience in the winter! The checkin and out process was well explained and simple. It is small though. It felt tight for our family if 3. I couldn’t imagine a group larger than that. Absolutely recommend for your small group. "
Located next to the Ski Resort, Bike Park and Water Park

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 €161
includes taxes & fees
29 Dec - 30 Dec
Cabin in the heart of the Hudson Valley, Cabin 4

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

9.4 out of 10, Exceptional, (30)
"Everything was good and we all enjoyed our stay"
The price is €548
includes taxes & fees
7 Jan - 8 Jan 2025
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

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

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.

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

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

Renovated 1850's Cottage on Storm King Mountain

9.8 out of 10, Exceptional, (15)
"This property offers something for everyone young and old. We would still be there if the availability worked out. Great experience!"
Renovated 1850's Cottage on Storm King Mountain

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

10.0 out of 10, Exceptional, (16)
"Property had lots of space for the kids to run around. The play set in the backyard was a big hit. We had plenty of room to hang out, play games or just talk. There is already talk about coming back in the summer. "
Luxury Retreat: Near Skiing, Hot Tub, Game Room, Playground! Pool in summer!

Rustic Chic at Mountain Creek! ❄️Slopes OPEN!❄️

10.0 out of 10, Exceptional, (43)
"i love the hotel i will use it whenever i go to vernon "
The price is €233
includes taxes & fees
13 Jan - 14 Jan 2025
Rustic Chic at Mountain Creek! ❄️Slopes OPEN!❄️

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is €369
includes taxes & fees
11 Jan - 12 Jan 2025
Contemporary Cozy Cottage
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, (1001)
"Good"
The price is €105
includes taxes & fees
1 Jan - 2 Jan 2025
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

DoubleTree by Hilton Hotel Nanuet

4.0 star property
8.6 out of 10, Excellent, (1003)
"nice people and polite and helpful highly recommended two thumbs up for sure will be back on this location."
The price is €127
includes taxes & fees
19 Jan - 20 Jan 2025
DoubleTree by Hilton Hotel Nanuet

Crowne Plaza Suffern - Mahwah, an IHG Hotel

3.5 star property
8.8 out of 10, Excellent, (1003)
"Nice rooms and hotel"
The price is €137
includes taxes & fees
29 Dec - 30 Dec
Crowne Plaza Suffern - Mahwah, an IHG Hotel
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.

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?

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!: This holiday home rental outside of Chester offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chester?

Expedia has 9 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 LEGOLAND® New York 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.