Chester Holiday Rentals

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Holiday Rentals in Chester

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Highland Falls
10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is AU$412
includes taxes & fees
8 Dec - 9 Dec
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls
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 AU$292
includes taxes & fees
15 Dec - 16 Dec
Cozy 1-bedroom retreat minutes from West Point!

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen
9.8 out of 10, Exceptional, (11)
"Overall Great"
United States
Nick H.
The price is AU$451
includes taxes & fees
11 Dec - 12 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Villa Verde B&B, bsm, Greenwood Lake NY

Greenwood Lake
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is AU$430
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY

Modern Hudson Valley Retreat Near Mohonk

2.0 star property
Plattekill
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
The price is AU$401
includes taxes & fees
7 Dec - 8 Dec
Modern Hudson Valley Retreat Near Mohonk

Cabin in the heart of the Hudson Valley, Cabin 3

Newburgh
9.8 out of 10, Exceptional, (14)
"We are moving to the area and found this cute place. Loved it and will stay here again. "
United States
Nicole G.
The price is AU$426
includes taxes & fees
10 Dec - 11 Dec
Cabin in the heart of the Hudson Valley, Cabin 3

Dream getaway apartment in the foot of Gunks Ridge

Wallkill
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 AU$306
includes taxes & fees
15 Dec - 16 Dec
Dream getaway apartment in the foot of Gunks Ridge

Grant - A Tranquil One Bedroom Steps from River

Newburgh
9.6 out of 10, Exceptional, (39)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
The price is AU$420
includes taxes & fees
29 Dec - 30 Dec
Grant - A Tranquil One Bedroom Steps from River

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

Warwick
9.4 out of 10, Exceptional, (6)
"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!"
United States
Jay D.
The price is AU$230
includes taxes & fees
6 Dec - 7 Dec
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Wallkill
10.0 out of 10, Exceptional, (70)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is AU$358
includes taxes & fees
7 Dec - 8 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is AU$372
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

2.5 star property
Vernon Township
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 AU$361
includes taxes & fees
7 Dec - 8 Dec
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
Westbrookville
The price is AU$466
includes taxes & fees
7 Dec - 8 Dec
Hike & Fish: Outdoor Retreat Near Trails

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Port Jervis
10.0 out of 10, Exceptional, (5)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
The price is AU$481
includes taxes & fees
7 Dec - 8 Dec
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is AU$426
includes taxes & fees
7 Dec - 8 Dec
Cabin in the Heart of the Hudson Valley, Cabin 1

Forava Cabins - Tiny Cabin in the Woods

3.0 star property
Ringwood
The price is AU$380
includes taxes & fees
7 Dec - 8 Dec
Forava Cabins - Tiny Cabin in the Woods

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is AU$469
includes taxes & fees
6 Dec - 7 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Hello Small Stone

Middletown
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is AU$679
includes taxes & fees
11 Dec - 12 Dec
Hello Small Stone

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls
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 AU$408
includes taxes & fees
9 Dec - 10 Dec
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Cozy country efficiency in the Hudson Valley

Newburgh
9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
The price is AU$504
includes taxes & fees
6 Dec - 7 Dec
Cozy country efficiency in the Hudson Valley
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 favourite 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 depend 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 AU$305 per night. Entering your travel dates in the search wizard might find you 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 a coffee maker, 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, Goosepond Mountain State Park and Museum Village 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.