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Chester Vacation 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 vacation 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 AED 509
AED 883 total
includes taxes & fees
17 Aug - 18 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 AED 551
AED 1,641 total
includes taxes & fees
16 Aug - 17 Aug
The DeVita House Est. 1900
Cottage (2 Bedrooms) | 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 AED 779
AED 1,897 total
includes taxes & fees
30 Aug - 31 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 AED 321
AED 562 total
includes taxes & fees
9 Sep - 10 Sep
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 AED 545
AED 1,089 total
includes taxes & fees
14 Aug - 15 Aug
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi (free), 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 AED 463
AED 1,018 total
includes taxes & fees
13 Aug - 14 Aug
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Design Apartment, Patio, Garden View | View from room

8. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is AED 1,123
AED 1,383 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 AED 606
AED 1,916 total
includes taxes & fees
30 Aug - 31 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Romantic Duplex, 3 Bedrooms, Kitchen | Private kitchen | Coffee/tea maker, toaster, cleaning supplies, freezer

10. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is AED 1,650
AED 2,032 total
includes taxes & fees
16 Aug - 17 Aug
Carriage House Apartment Goshen NY
Apartment, 3 Bedrooms, Kitchen | Living area

11. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is AED 1,616
AED 1,989 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 AED 397
AED 785 total
includes taxes & fees
2 Sep - 3 Sep
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 AED 645
AED 1,074 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 AED 362
AED 792 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 AED 311
AED 551 total
includes taxes & fees
9 Sep - 10 Sep
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 AED 459
AED 1,305 total
includes taxes & fees
12 Aug - 13 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 AED 496
AED 1,084 total
includes taxes & fees
24 Aug - 25 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 AED 642
AED 1,169 total
includes taxes & fees
12 Aug - 13 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 AED 727
AED 1,224 total
includes taxes & fees
17 Aug - 18 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 AED 474
AED 733 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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"Outside of the room, it looks rundown but once in the room, it was fine. It was perfect for a couple of nights. Bed was crisp and comfy. But the walls are thin and you can hear everything in the hallway. I didn't have breakfast but I checked it out and it had a very small selection: hard boiled eggs, bagels, mini muffins, toast, cereal & yogurt. Coffee was alright. A little on the weak side for my taste."
Karina 2-night trip
Posted less than an hour ago
Spark by Hilton Fishkill

Frequently asked questions

Are there vacation rentals in Chester?

Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.

What are some of the best vacation home rentals in Chester?

Cozy Cabin with Sauna & Firepit!: This vacation home rental near Chester offers a fireplace, a barbecue grill, 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 vacation rentals are there in Chester?

Expedia has 11 vacation 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 favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.