Chester Holiday Rentals

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Our top choices for Chester holiday rentals

10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$325
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$264
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is NZ$404
includes taxes & fees
7 Jan - 8 Jan 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
The price is NZ$426
includes taxes & fees
7 Jan - 8 Jan 2026
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is NZ$284
includes taxes & fees
4 Jan - 5 Jan 2026
Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is NZ$444
includes taxes & fees
30 Dec - 31 Dec
Grant - A Tranquil One Bedroom Steps from River
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is NZ$770
includes taxes & fees
12 Jan - 13 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (46)
"i love the hotel i will use it whenever i go to vernon "
United States
Michael P.
The price is NZ$497
includes taxes & fees
6 Jan - 7 Jan 2026
Lifts OPEN! Rustic Chic at Mountain Creek! Heated Outdoor Pool, Hot Tubs, Sauna
2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is NZ$749
includes taxes & fees
30 Dec - 31 Dec
Stylish & Peaceful Getaway on 3 Private Acres
10.0 out of 10, Exceptional, (42)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
The price is NZ$419
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$456
includes taxes & fees
20 Jan - 21 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.2 out of 10, Wonderful, (25)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is NZ$342
includes taxes & fees
30 Dec - 31 Dec
Cabin in the heart of the Hudson Valley, Cabin 4
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is NZ$501
includes taxes & fees
30 Dec - 31 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
10.0 out of 10, Exceptional, (26)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is NZ$439
includes taxes & fees
30 Dec - 31 Dec
The Wine House, Sitting atop of Warwick's brand new Wine Bar
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
The price is NZ$429
includes taxes & fees
27 Jan - 28 Jan 2026
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
10.0 out of 10, Exceptional, (33)
"The place was beautiful. Would highly recommended staying here. "
United States
Ranada
The price is NZ$505
includes taxes & fees
5 Jan - 6 Jan 2026
2 bedroom cozy condo with parking on premises
9.6 out of 10, Exceptional, (50)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is NZ$542
includes taxes & fees
4 Jan - 5 Jan 2026
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.8 out of 10, Exceptional, (15)
"So clean and spacious! Everything was great "
United States
Dorene W.
The price is NZ$463
includes taxes & fees
30 Dec - 31 Dec
Modern Hudson Valley Apt 202 - King/Queen/Twin
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is NZ$481
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as NZ$406 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Chester?

Expedia has 10 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. While here, Museum Village and Goosepond Mountain State Park are other places worth a visit.

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.