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Chester Vacation Rentals

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Check prices for these dates

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

Our top choices for Chester vacation rentals

A hot tub with a wooden deck and railing, surrounded by a grassy area and a stone wall.

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 ￥300,720
￥467,161 total
includes taxes & fees
Sep 27 - Sep 28
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

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
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

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 ￥14,129
￥27,655 total
includes taxes & fees
Oct 13 - Oct 14
Cottage Suites
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

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 ￥14,014
￥24,394 total
includes taxes & fees
Sep 28 - Sep 29
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

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 ￥23,356
￥44,128 total
includes taxes & fees
Oct 4 - Oct 5
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

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 ￥15,716
￥38,613 total
includes taxes & fees
Sep 28 - Sep 29
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A hot tub in a lush garden with a stone wall and outdoor furniture.

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 ￥51,745
￥89,524 total
includes taxes & fees
Oct 27 - Oct 28
Country House w/Hot Tub, Deck, Grill & Fire Pit
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

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 ￥16,974
￥35,430 total
includes taxes & fees
Sep 29 - Sep 30
Historic Cabin with Pool & Fire Pit
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

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 ￥88,706
￥135,607 total
includes taxes & fees
Oct 27 - Oct 28
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

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 ￥27,603
￥43,683 total
includes taxes & fees
Sep 27 - Sep 28
The Wine House
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

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 ￥36,174
￥44,482 total
includes taxes & fees
Oct 27 - Oct 28
Villa Verde B&B, bsm, Greenwood Lake NY
A two-story house with a porch, a table, and chairs outside.

12. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is ￥48,196
￥59,341 total
includes taxes & fees
Oct 3 - Oct 4
Historic Horse Barn Apartment in Goshen
A room with a chandelier, a sofa, a table, and a cabinet.

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 ￥15,288
￥25,916 total
includes taxes & fees
Oct 7 - Oct 8
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

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 ￥23,592
￥48,041 total
includes taxes & fees
Oct 14 - Oct 15
Charming 2-bedroom apartment in the Village of Warwick
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

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 ￥24,971
￥48,672 total
includes taxes & fees
Sep 27 - Sep 28
Modern Hudson Valley Apt 202 - King/Queen/Twin
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

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 ￥55,048
￥111,101 total
includes taxes & fees
Oct 14 - Oct 15
Amazing Home Near West Point, Shopping, Skiing and Legoland
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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 ￥19,660
￥59,530 total
includes taxes & fees
Sep 28 - Sep 29
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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 ￥18,256
￥45,979 total
includes taxes & fees
Sep 27 - Sep 28
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A hot tub with a view of a lake and houses in the background.

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 ￥34,925
￥85,482 total
includes taxes & fees
Sep 29 - Sep 30
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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 ￥16,986
￥39,151 total
includes taxes & fees
Sep 28 - Sep 29
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 2 hours ago
Hilton Garden Inn Nanuet

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 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.