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Chester Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chester holiday rentals

Outdoor dining

1. Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub
Chester
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay! The house was even better than the pictures. There was plenty of space for our large group, and the 10 bedrooms made it comfortable for everyone. The pool and hot tub were definitely highlights, and the game room kept both the kids and adults entertained throughout the trip.One of the things we loved most was how private and secluded the property felt. It was the perfect place to relax, unwind, and spend quality time together without feeling crowded. The home was clean,...
United States
Jacob F.
Serene 10BR Retreat w/Pool, Gym & Hot Tub
Property grounds

2. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (14 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$1,087
HK$1,894 total
includes taxes & fees
11 Aug - 12 Aug
TRANQUIL MOUNTAIN SOLITUDE
Smart TV

3. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (37 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is HK$1,177
HK$3,506 total
includes taxes & fees
16 Aug - 17 Aug
The DeVita House Est. 1900
Interior

4. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is HK$1,663
HK$4,053 total
includes taxes & fees
11 Aug - 12 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Interior

5. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is HK$685
HK$1,201 total
includes taxes & fees
9 Sept - 10 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV

6. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is HK$1,165
HK$2,295 total
includes taxes & fees
14 Aug - 15 Aug
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, free WiFi, bed sheets

7. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (45 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is HK$988
HK$2,183 total
includes taxes & fees
13 Aug - 14 Aug
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
View from room

8. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is HK$2,436
HK$2,999 total
includes taxes & fees
19 Aug - 20 Aug
Historic Horse Barn Apartment in Goshen
TV, fireplace, DVD player

9. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (8 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is HK$1,294
HK$4,127 total
includes taxes & fees
11 Aug - 12 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Private kitchen

10. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is HK$3,615
HK$4,451 total
includes taxes & fees
16 Aug - 17 Aug
Carriage House Apartment Goshen NY
Living area

11. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is HK$3,451
HK$4,249 total
includes taxes & fees
17 Aug - 18 Aug
Hay Loft Apartment in Barn - Goshen
Exterior

12. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$881
HK$1,742 total
includes taxes & fees
1 Sept - 2 Sept
Historic Cabin with Pool & Fire Pit
Coffee/tea maker, fridge, microwave, oven

13. The Wine House, Sitting atop of Warwick's brand new Wine Bar

The Wine House, Sitting atop of Warwick's brand new Wine Bar
Warwick
10.0 out of 10, Exceptional, (35 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is HK$1,377
HK$2,276 total
includes taxes & fees
12 Aug - 13 Aug
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Property grounds

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

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (92 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is HK$774
HK$1,666 total
includes taxes & fees
16 Aug - 17 Aug
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

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

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.4 out of 10, Very good, (15 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is HK$664
HK$1,177 total
includes taxes & fees
9 Sept - 10 Sept
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

16. Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"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 HK$981
HK$2,930 total
includes taxes & fees
11 Aug - 12 Aug
Hello Small Stone
Smart TV

17. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is HK$1,059
HK$2,325 total
includes taxes & fees
17 Aug - 18 Aug
Grant - A Tranquil One Bedroom Steps from River
Microwave, oven, stovetop, dishwasher

18. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is HK$1,372
HK$2,569 total
includes taxes & fees
11 Aug - 12 Aug
Modern Hudson Valley Apt 202 - King/Queen/Twin
Property grounds

19. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,553
HK$2,558 total
includes taxes & fees
11 Aug - 12 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining

20. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is HK$1,012
HK$1,575 total
includes taxes & fees
12 Aug - 13 Aug
Cabin in the heart of the Hudson Valley, Cabin 4
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Central"
JONATHAN 2-night trip
Posted 2 hours ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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 Cabin with Sauna & Firepit!: This holiday home rental outside of Chester offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave.

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?

Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. 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.