Photo by Kristin Patton

Chester Holiday Rentals

    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

Charming 2-bedroom house on 2 dog friendly landscaped acres in lovely Chester

2.0 star property
10.0 out of 10, Exceptional, (8)
"We stayed one week and loved this home. The grounds are beautiful and our dogs loved the space. The house was perfect for us. "
Charming 2-bedroom house on 2 dog friendly landscaped acres in lovely Chester

1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths

10.0 out of 10, Exceptional, (29)
"This beautiful house, in a beautiful neighborhood, was a perfect fit for our large extended family get-together! Including everything from the many bedrooms and bathrooms, to the large gathering spaces, and well-equipped kitchen! "
1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths

New Modern Ranch Close to it All

6.6 out of 10, (4)
"Well-maintainedNice amenities"
New Modern Ranch Close to it All

Madison Home: Walk to Main Street!

2.0 star property
8.8 out of 10, Excellent, (17)
"Highly recommended "
Madison Home: Walk to Main Street!

Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ

9.4 out of 10, Exceptional, (6)
"Fantastic and cozy lake house, with quick access to the lake. Clean property with all the amenities, and close by local shops and attractions. Owner was very curteous, and the kayaks were a nice way to access the water :) Overall a wonderful stay for an affordable cost"
The price is NZ$744
includes taxes & fees
12 Aug - 13 Aug
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ

BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom

9.2 out of 10, Wonderful, (15)
"Catalina, the host, was always helpful and so considerate and made sure we had everything we needed. The house was clean and the neighborhood was very safe. My friends and I enjoyed our stay, I would totally stay here again!"
The price is NZ$1,890
includes taxes & fees
20 July - 21 July
BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom

New Renovated vacation house

10.0 out of 10, Exceptional, (45)
"Our group had an amazing time, The house is as advertised and the host is extremely attentive and responsive. "
New Renovated vacation house

MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)

7.4 out of 10, Good, (6)
"It was nice and would be a steal for a few couples combined)."
The price is NZ$427
includes taxes & fees
20 July - 21 July
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)

Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

10.0 out of 10, Exceptional, (33)
"Great communication - beautiful property - highly recommend!"
The price is NZ$6,266
includes taxes & fees
22 July - 23 July
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

Family Farm Estate: Private Outdoor Paradise with Two Houses, Pond, & Golf Range

10.0 out of 10, Exceptional, (4)
"Enjoyed the amenities, we used the peddle boat and row boat and hits some golf balls. Wish we had time for all the other amenities offered. "
Family Farm Estate: Private Outdoor Paradise with Two Houses, Pond, & Golf Range

Home Away From Home -- with pools, parks, hiking, fishing, and lakes nearby!

9.0 out of 10, Wonderful, (2)
"Home was well appointed for out-of-town family visiting."
The price is NZ$718
includes taxes & fees
19 July - 20 July
Home Away From Home -- with pools, parks, hiking, fishing, and lakes nearby!

Charming 2-bedroom apartment with WiFi, AC in tranquil Morristown

8.8 out of 10, Excellent, (10)
"The property was very nice and very convenient to all the areas we traveled to. If we have the opportunity to return we hope we will be able to book this place again. Thanks"
Charming 2-bedroom apartment with WiFi, AC in tranquil Morristown

Charming Apartment in Flemington

10.0 out of 10, Exceptional, (13)
"Apartment and its location were great. Highly recommend."
Charming Apartment in Flemington

Entire Private Lakefront Cottage Home on Lake Hopatcong + Kayaks and Pedalboat

9.8 out of 10, Exceptional, (43)
"After a long day of work the home was the perfect retreat."
Entire Private Lakefront Cottage Home on Lake Hopatcong + Kayaks and Pedalboat

Cozy Cabin with Hot Tub, Private Lake & Game Room

9.4 out of 10, Exceptional, (14)
"Property exactly as described, in a great location. Easy communication with host. Would definitely stay again if returning to the area."
Cozy Cabin with Hot Tub, Private Lake & Game Room

Historic Country Estate with Fabulous Pool & Pool House!

10.0 out of 10, Exceptional, (36)
"Excellent in every way "
Historic Country Estate with Fabulous Pool & Pool House!

Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck

9.6 out of 10, Exceptional, (5)
"Bathroom tub/shower needs renovation"
Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck

Luxury Log Cabin w/ EV Charger & Mtn Views!

9.8 out of 10, Exceptional, (10)
"We enjoyed the house. The kitchen was very nicely equipped. "
Luxury Log Cabin w/ EV Charger & Mtn Views!

LAKEFRONT Level Lot Home with a Private Deck/Dock w/ 2 Kayaks & Paddle Boards

10.0 out of 10, Exceptional, (4)
"Perfect if you are looking for a quiet getaway"
LAKEFRONT Level Lot Home with a Private Deck/Dock w/ 2 Kayaks & Paddle Boards

The Luxury modern home with pool

10.0 out of 10, Exceptional, (18)
"We were able to stay in this beautiful home for one evening. What a stay it was, the house is as modern as advertised and as clean as a whistle. Next time we get together we’re for sure going to look forward to this venue."
The Luxury modern home with pool
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

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Alstede Farms, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its shopping and restaurants. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Chester has to offer?

1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths : This holiday home rental outside of Chester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Chester?

Chubb Park and Kay Environmental Center are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Alstede Farms and Hacklebarney State Park.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips or small group gatherings.