Chester Holiday Rentals

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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 NZ$525
includes taxes & fees
30 Sept - 1 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 NZ$514
includes taxes & fees
3 Oct - 4 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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

9.6 out of 10, Exceptional, (35)
"Great place for a quiet stay"
The price is NZ$564
includes taxes & fees
12 Oct - 13 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

10.0 out of 10, Exceptional, (308)
"Fortunate to have found the time to spend a long weekend by the lake. Just the right remedy for our usual fast-paced schedules. Caught a beautiful sunset the first evening but every day was just as enjoyable."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

10.0 out of 10, Exceptional, (50)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is NZ$456
includes taxes & fees
29 Sept - 30 Sept
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (22)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is NZ$817
includes taxes & fees
30 Sept - 1 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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

9.8 out of 10, Exceptional, (12)
"This property has exactly what we were looking for to spend a long weekend and create new memories. The welcoming atmosphere and breathtaking views offer a unique experience. Jones was easily accessible to respond to any questions. We will certainly come and definitely recommend this property to family and friends. "
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

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

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is NZ$492
includes taxes & fees
30 Sept - 1 Oct
A luxurious stay.

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

10.0 out of 10, Exceptional, (4)
"This property was comfortable, quaint and clean. Perfect little weekend getaway. We definitely plan on staying here again. "
The price is NZ$424
includes taxes & fees
29 Sept - 30 Sept
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

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 NZ$647
includes taxes & fees
13 Oct - 14 Oct
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

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 NZ$712
includes taxes & fees
8 Oct - 9 Oct
Rustic Cabin in Fishkill!

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

9.4 out of 10, Exceptional, (39)
"The rental was lovely. We all went up for friends wedding great location and am going back to check out the alien museum. "
The price is NZ$734
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

10.0 out of 10, Exceptional, (2)
"Beautiful home, on a quiet street. Ample view from the living room, kitchen and deck/dock. We loved have a little private beach area for my daughter. The game room was such a fun bonus!! We will definitely be back !! "
The price is NZ$896
includes taxes & fees
22 Oct - 23 Oct
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

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 NZ$332
includes taxes & fees
28 Sept - 29 Sept
Romantic spot above restaurant., ideal for the gourmet

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

10.0 out of 10, Exceptional, (66)
"We had a great stay."
The price is NZ$498
includes taxes & fees
29 Sept - 30 Sept
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (142)
"We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!"
Greenwood Lake Lakefront Luxury

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is NZ$1,155
includes taxes & fees
26 Sept - 27 Sept
Large,Cozy,Bright Apartment, Business Themed.

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 NZ$987
includes taxes & fees
29 Sept - 30 Sept
Chestnut on Willow Lake

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.4 out of 10, Exceptional, (25)
"A fantastic little getaway after a wonderful day of hiking the Catskills! Vinny & Josh were perfect hosts and the property is fantastic! Will definitely be back! "
The price is NZ$326
includes taxes & fees
28 Sept - 29 Sept
Cozy Loft Cabin high above Bashakill Wildlife Refuge
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, 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 NZ$326 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?

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 11 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.