Holiday Rentals in Chester

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Holiday Rentals in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is €268
includes taxes & fees
13 Oct - 14 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

9.4 out of 10, Exceptional, (38)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
The price is €265
includes taxes & fees
5 Oct - 6 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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

10.0 out of 10, Exceptional, (51)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is €231
includes taxes & fees
2 Oct - 3 Oct
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

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

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is €290
includes taxes & fees
1 Nov - 2 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

8.6 out of 10, Excellent, (87)
"Wish we could have stayed longer. Great place and lots of room for your whole family. "
The price is €363
includes taxes & fees
5 Oct - 6 Oct
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

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

10.0 out of 10, Exceptional, (33)
"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!"
The price is €303
includes taxes & fees
13 Oct - 14 Oct
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is €504
includes taxes & fees
2 Oct - 3 Oct
Chestnut on Willow Lake

Located next to the Ski Resort, Bike Park and Water Park

9.8 out of 10, Exceptional, (170)
"Family lives in Warwick NY & this was the perfect distance from their home! Kristof & Barbara were awesome hosts & their condo was great!!"
Located next to the Ski Resort, Bike Park and Water Park

Houseboat Paradise Vacation

2.0 star property
The price is €575
includes taxes & fees
2 Oct - 3 Oct
Houseboat Paradise Vacation

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

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is €312
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (16)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is €461
includes taxes & fees
21 Oct - 22 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

The Woodbury Cottage

8.8 out of 10, Excellent, (25)
"A cozy place to stay. "
The Woodbury Cottage

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

9.8 out of 10, Exceptional, (86)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (3)
"Hosts communicated well, the room was spacious and clean, and the restaurant downstairs is spectacular. "
The price is €168
includes taxes & fees
27 Oct - 28 Oct
Romantic spot above restaurant., ideal for the gourmet

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is €595
includes taxes & fees
5 Oct - 6 Oct
Large,Cozy,Bright Apartment, Business Themed.

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (39)
"Very nice location and spacious house.Bbq grill could be better"
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
The price is €853
includes taxes & fees
28 Oct - 29 Oct
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
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

Find out more about Chester

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as €168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out: This holiday home rental outside of Chester is located in the mountains, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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.