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Chester Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chester holiday 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 HK$19,391
HK$30,569 total
includes taxes & fees
30 Sept - 1 Oct
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
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)
The price is HK$3,044
HK$3,748 total
includes taxes & fees
2 Oct - 3 Oct
Hay Loft Apartment in Barn - Goshen
Outdoor spa tub

3. 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$2,580
HK$4,543 total
includes taxes & fees
28 Sept - 29 Sept
Country House w/Hot Tub, Deck, Grill & Fire Pit
Property grounds

4. 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$7,147 total
includes taxes & fees
21 Sept - 22 Sept
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
View from room

5. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is HK$2,706
HK$3,332 total
includes taxes & fees
2 Oct - 3 Oct
Historic Horse Barn Apartment in Goshen
Coffee/tea maker, fridge, microwave, oven

6. 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$5,615 total
includes taxes & fees
28 Sept - 29 Sept
Amazing Home Near West Point, Shopping, Skiing and Legoland
Interior

7. 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$713
HK$1,233 total
includes taxes & fees
29 Sept - 30 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV

8. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 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
24 Sept - 25 Sept
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

9. Mountain View Retreat w/ Hot Tub, Theater, and Gym

Mountain View Retreat w/ Hot Tub, Theater, and Gym
Warwick
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay on a beautiful place!"
United States
Dorian G.
The price is HK$5,359
HK$10,427 total
includes taxes & fees
17 Sept - 18 Sept
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Outdoor spa tub

10. 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$1,751
HK$4,093 total
includes taxes & fees
17 Sept - 18 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Coffee/tea maker, fridge, microwave, oven

11. 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$2,276 total
includes taxes & fees
22 Sept - 23 Sept
The Wine House
1 bedroom, free WiFi, bed sheets

12. 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$769
HK$1,900 total
includes taxes & fees
22 Sept - 23 Sept
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Exterior

13. Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,647
HK$4,210 total
includes taxes & fees
27 Sept - 28 Sept
Modern penthouse suite in a restored grain tower with private roof deck.
Coffee/tea maker, fridge, microwave, oven

14. Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is HK$2,345
HK$4,020 total
includes taxes & fees
17 Sept - 18 Sept
Luxury 3BR with King Beds in Montgomery Village
Property grounds

15. Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is HK$1,804
HK$2,804 total
includes taxes & fees
17 Sept - 18 Sept
Villa Verde B&B, Greenwood Lake NY, 1
Exterior detail

16. 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$2,520 total
includes taxes & fees
23 Sept - 24 Sept
Charming 2-bedroom apartment in the Village of Warwick
Interior

17. 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$2,263 total
includes taxes & fees
1 Oct - 2 Oct
Villa Verde B&B, bsm, Greenwood Lake NY
Coffee/tea maker, fridge, oven, stovetop

18. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is HK$1,584
HK$3,656 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Microwave, oven, stovetop, dishwasher

19. 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$2,313 total
includes taxes & fees
20 Sept - 21 Sept
Modern Hudson Valley Apt 202 - King/Queen/Twin
Outdoor spa tub

20. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (14 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is HK$1,655
HK$3,308 total
includes taxes & fees
29 Sept - 30 Sept
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"Great stay and location."
dave 2-night trip
Posted 5 hours ago
Comfort Suites Fishkill near Interstate 84

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.