Holiday Rentals in Chester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Chester

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (302)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is €527
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

9.8 out of 10, Exceptional, (28)
"Jose has a wonderful home! Beautiful and quiet stay in a well-equipped spaced. My family had a lovely time. "
The price is €290
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

10.0 out of 10, Exceptional, (47)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is €242
includes taxes & fees
25 Aug - 26 Aug
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

8.6 out of 10, Excellent, (85)
"Wish we could have stayed longer. Great place and lots of room for your whole family. "
The price is €392
includes taxes & fees
1 Sept - 2 Sept
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is €501
includes taxes & fees
15 Sept - 16 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Cottage Suites

3.0 star property
6.6 out of 10, (7)
"It was a great place "
Cottage Suites

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

10.0 out of 10, Exceptional, (62)
"Beautiful views!"
The price is €268
includes taxes & fees
18 Aug - 19 Aug
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (119)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is €281
includes taxes & fees
1 Sept - 2 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (9)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is €154
includes taxes & fees
19 Aug - 20 Aug
Cabin in the heart of the Hudson Valley, Cabin 2

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (29)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (2)
"Highly recommended! Such a vibe, quiet & cozy. You can hear the birds in the morning, so peaceful. I would go back!! "
The price is €171
includes taxes & fees
17 Aug - 18 Aug
Romantic spot above restaurant., ideal for the gourmet

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.4 out of 10, Exceptional, (36)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
The price is €268
includes taxes & fees
21 Aug - 22 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Luxurious/Private-Heated pool, Hot tub & Tennis/Golf/Ski in-Ski Out Mnt. Creek

9.8 out of 10, Exceptional, (83)
"Amazing property for a large get together of family and friends! Kitchen is well stocked. Legos and games to keep children entertained! House was clean and had plenty of space. We came to ski but would consider coming back for other seasons as well "
Luxurious/Private-Heated pool, Hot tub & Tennis/Golf/Ski in-Ski Out Mnt. Creek

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is €159
includes taxes & fees
19 Aug - 20 Aug
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Cabin in the heart of the Hudson Valley, Cabin 4

9.2 out of 10, Wonderful, (25)
"Exactly as advertised "
The price is €154
includes taxes & fees
19 Aug - 20 Aug
Cabin in the heart of the Hudson Valley, Cabin 4

Private lake escape

Private lake escape

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

10.0 out of 10, Exceptional, (23)
"Wonderful stay!"
The price is €473
includes taxes & fees
18 Aug - 19 Aug
Modern penthouse suite in a restored grain tower with private roof deck.

Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

9.0 out of 10, Wonderful, (6)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

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. You’ll find favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

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.