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Chester Holiday 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 holiday 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 HK$15,582
HK$23,983 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$698
HK$1,367 total
includes taxes & fees
13 Oct - 14 Oct
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 HK$699
HK$1,217 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$1,165
HK$2,201 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$777
HK$1,855 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$2,581
HK$4,465 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$839
HK$1,732 total
includes taxes & fees
29 Sept - 30 Sept
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 HK$4,424
HK$6,763 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$1,377
HK$2,179 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$1,804
HK$2,218 total
includes taxes & fees
1 Oct - 2 Oct
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
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 HK$755
HK$1,281 total
includes taxes & fees
7 Oct - 8 Oct
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 HK$1,177
HK$2,396 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$1,234
HK$2,303 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$2,745
HK$5,504 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$981
HK$2,969 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$902
HK$2,272 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$1,639
HK$3,869 total
includes taxes & fees
29 Sept - 30 Sept
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 HK$839
HK$1,881 total
includes taxes & fees
28 Sept - 29 Sept
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The room was a little warm. There was no way to make it cooler."
Marilyn 1-night trip
Posted 3 hours ago
Overlook Lodge at Bear Mountain

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

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. While here, Castle Fun Center and Goosepond Mountain State Park 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.