Chester Holiday Rentals

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Check prices for these dates

Tonight
16 Jan - 17 Jan
Tomorrow
17 Jan - 18 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Chester holiday rentals

Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (54 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is HK$1,930
HK$2,466 total
includes taxes & fees
17 Jan - 18 Jan
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,754
HK$3,228 total
includes taxes & fees
25 Jan - 26 Jan
Contemporary Cozy Cottage
Property grounds

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$1,224
HK$2,046 total
includes taxes & fees
13 Feb - 14 Feb
Villa Verde B&B, Greenwood Lake NY, 1
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (46 reviews)
"Great place!"
United States
Sara B.
The price is HK$1,014
HK$2,047 total
includes taxes & fees
21 Jan - 22 Jan
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$858
HK$1,822 total
includes taxes & fees
20 Jan - 21 Jan
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds

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, (129 reviews)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is HK$1,466
HK$2,373 total
includes taxes & fees
19 Jan - 20 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor spa tub

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (59 reviews)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is HK$1,930
HK$3,904 total
includes taxes & fees
20 Jan - 21 Jan
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Smart TV, fireplace

Golf Front | Mountain Views | Updated | Modern

Golf Front | Mountain Views | Updated | Modern
Vernon
9.6 out of 10, Exceptional, (5 reviews)
"We had a very nice stay here. Beautifully decorated. We ran into a couple issues which were immediately resolved by the owner."
United States
Kate S.
The price is HK$1,392
HK$3,028 total
includes taxes & fees
25 Jan - 26 Jan
Golf Front | Mountain Views | Updated | Modern
Exterior

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, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,632
HK$4,159 total
includes taxes & fees
19 Jan - 20 Jan
Modern penthouse suite in a restored grain tower with private roof deck.
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$585
HK$2,010 total
includes taxes & fees
19 Jan - 20 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Vernon
10.0 out of 10, Exceptional, (73 reviews)
"Great stay"
United States
cristina g.
The price is HK$1,046
HK$2,177 total
includes taxes & fees
19 Jan - 20 Jan
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (66 reviews)
"Such a cute place to stay"
United States
Melissa
The price is HK$1,365
HK$2,542 total
includes taxes & fees
17 Jan - 18 Jan
Cozy country efficiency in the Hudson Valley
Pool

Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M

Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M
vernon
10.0 out of 10, Exceptional, (15 reviews)
"Great place to stay, excellent location."
United States
Jacob B.
The price is HK$1,637
HK$3,414 total
includes taxes & fees
22 Jan - 23 Jan
Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M
Dining

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340
Vernon
10.0 out of 10, Exceptional, (19 reviews)
"An excellent hotel "
United States
Galyna
The price is HK$1,122
HK$2,370 total
includes taxes & fees
28 Jan - 29 Jan
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24 reviews)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is HK$453
HK$1,291 total
includes taxes & fees
21 Jan - 22 Jan
Dream getaway apartment in the foot of Gunks Ridge
Golf

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
Vernon Township
10.0 out of 10, Exceptional, (31 reviews)
"Great time great location"
United States
R J.
The price is HK$1,365
HK$2,634 total
includes taxes & fees
20 Jan - 21 Jan
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is HK$1,187
HK$2,396 total
includes taxes & fees
20 Jan - 21 Jan
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
Vernon Township
10.0 out of 10, Exceptional, (10 reviews)
"This property was comfortable, quaint and clean. Perfect little weekend getaway. We definitely plan on staying here again. "
United States
Mandi
The price is HK$1,326
HK$2,521 total
includes taxes & fees
19 Jan - 20 Jan
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
Smart TV

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)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is HK$1,158
HK$2,297 total
includes taxes & fees
20 Jan - 21 Jan
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Terrace/patio

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$710
HK$2,715 total
includes taxes & fees
22 Jan - 23 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!
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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Staff was awesome. Room was great. Pool and hot tub very clean. Hot tub didn’t feel disgusting like a lot of places. "
Ava 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel 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 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Chester?

Expedia has 10 holiday rentals for your stay in Chester.

What can I see and do in Chester?

Family-friendly attractions include Castle Fun Center, whereas The Rock Sports Complex is a spot to enjoy the outdoors. While here, Goosepond Mountain State Park and Museum Village 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.