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Chester Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chester vacation rentals

Outdoor spa tub

1. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
10.0 out of 10, Exceptional, (2 reviews)
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"
United States
Benny P.
The price is AED 6,958
AED 10,809 total
includes taxes & fees
27 Sep - 28 Sep
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Apartment, 3 Bedrooms, Kitchen | Living area

2. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Hay Loft Apartment in Barn - Goshen
Suite | Desk, WiFi (free), individually furnished, bed sheets

3. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.4 out of 10, (18 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is AED 327
AED 640 total
includes taxes & fees
13 Oct - 14 Oct
Cottage Suites
Interior

4. 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
8.6 out of 10, Excellent, (19 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 327
AED 570 total
includes taxes & fees
28 Sep - 29 Sep
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV

5. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,075 total
includes taxes & fees
27 Sep - 28 Sep
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi (free), bed sheets

6. 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, (47 reviews)
"In the area for my nephew’s graduation. Loved walking around Warwick and checking out shops.Beautiful accommodations. Very clean, easy check in, comfortable bed. Appreciated the options for coffee and tea. Overall, a great stay."
United States
Gwenda M.
The price is AED 364
AED 868 total
includes taxes & fees
27 Sep - 28 Sep
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Outdoor spa tub

7. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (67 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is AED 1,208
AED 2,091 total
includes taxes & fees
27 Sep - 28 Sep
Country House w/Hot Tub, Deck, Grill & Fire Pit
Exterior

8. 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 393
AED 811 total
includes taxes & fees
29 Sep - 30 Sep
Historic Cabin with Pool & Fire Pit
Property grounds

9. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is AED 2,072
AED 3,222 total
includes taxes & fees
27 Sep - 28 Sep
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Coffee/tea maker, fridge, microwave, oven

10. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (38 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
The price is AED 645
AED 1,020 total
includes taxes & fees
27 Sep - 28 Sep
The Wine House
Interior

11. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
The price is AED 845
AED 1,039 total
includes taxes & fees
1 Oct - 2 Oct
Villa Verde B&B, bsm, Greenwood Lake NY
Design Apartment, Patio, Garden View | View from room

12. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is AED 1,128
AED 1,389 total
includes taxes & fees
3 Oct - 4 Oct
Historic Horse Barn Apartment in Goshen
Interior

13. 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
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is AED 354
AED 600 total
includes taxes & fees
7 Oct - 8 Oct
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior detail

14. Charming 2-bedroom apartment in the Village of Warwick

Charming 2-bedroom apartment in the Village of Warwick
Warwick
9.4 out of 10, Exceptional, (3 reviews)
"Clean, family friendly, close to everything."
United States
Milena P.
The price is AED 551
AED 1,122 total
includes taxes & fees
30 Sep - 1 Oct
Charming 2-bedroom apartment in the Village of Warwick
Microwave, oven, stovetop, dishwasher

15. 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)
"Great hosts and great location!"
United States
Shelby A.
The price is AED 578
AED 1,078 total
includes taxes & fees
27 Sep - 28 Sep
Modern Hudson Valley Apt 202 - King/Queen/Twin
Coffee/tea maker, fridge, microwave, oven

16. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
The price is AED 1,286
AED 2,577 total
includes taxes & fees
30 Sep - 1 Oct
Amazing Home Near West Point, Shopping, Skiing and Legoland
Terrace/patio

17. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (12 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is AED 459
AED 1,390 total
includes taxes & fees
27 Sep - 28 Sep
House on the Babbling Brook- Quiet 2BR + King Bed!
Coffee/tea maker, fridge, oven, stovetop

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 422
AED 1,064 total
includes taxes & fees
27 Sep - 28 Sep
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Outdoor spa tub

19. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (41 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is AED 808
AED 1,978 total
includes taxes & fees
29 Sep - 30 Sep
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Interior

20. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (52 reviews)
"One of the cleanest VRBOs I ever stayed in - it smelled so good. Very cozy and had everything we needed. The location is great!"
United States
Tara K.
The price is AED 393
AED 881 total
includes taxes & fees
28 Sep - 29 Sep
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
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

Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

8/10 Good
"Clean place and good breakfast"
Stacy 1-night trip
Posted 8 hours ago
Hilton Garden Inn Nanuet

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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental near Chester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. While here, Castle Fun Center and Goosepond Mountain State Park are other places worth a visit.

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.