Photo by Kristin Patton

Chester Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

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, (4)
"Great communication. Beautiful property, convenient to center of Chester. Clean home. Host very accommodating."
Charming 2-bedroom house on 2 dog friendly landscaped acres in lovely Chester

Stay at beautiful Leisure Lake Lodge

10.0 out of 10, Exceptional, (126)
"House was nice but no mention of tons of stairs to actually gain access to property was deceptive from property details. We should have asked owner PRIOR to making the rez, as we clear on having an elderly dog, who struggled to get up/down all the stairs. Lugging all our stuff in/out was a hardship as well. Mid way thru our stay we had a random person put a key in door and barge into the home with an attitude, saying they were an "associate" of the owner, and we were supposed to be checked out...
Stay at beautiful Leisure Lake Lodge

Lake house

The price is AU$1,073
includes taxes & fees
3 Feb - 4 Feb
Lake house

Madison Home: Walk to Main Street!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Host was so friendly and welcoming! My friends and I enjoyed talking with him and learning about his Italian family history; it was very interesting. The home is clean and has lots of space. room.Wenjoyed the lowimultiplec"
Madison Home: Walk to Main Street!

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, (22)
"This property excelled past my expectations. The pictures and descriptions is exactly as described. Its spacious enough to not feel like everyone is confined in one location. The home offers various things to do. It was perfect. "
1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths

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

10.0 out of 10, Exceptional, (33)
"Outstanding!"
The price is AU$5,107
includes taxes & fees
3 Feb - 4 Feb
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

223 Brand New 2 Bdrm, 2 BATH, 1 Liv, 1 Kith

10.0 out of 10, Exceptional, (1)
"Painless process to check in. Property was clean and cozy. Definitely recommend!"
The price is AU$456
includes taxes & fees
3 Feb - 4 Feb
223 Brand New 2 Bdrm, 2 BATH, 1 Liv, 1 Kith

Beautiful Lakefront Retreat w/ Deck & Views!

9.0 out of 10, Wonderful, (16)
"Lovely home and great alternative with a lack of hotels in the area. Everything we needed. "
Beautiful Lakefront Retreat w/ Deck & Views!

The Celebration Stay: Perfect for friends & family

The Celebration Stay: Perfect for friends & family

Historic Country Estate with Fabulous Pool & Pool House!

10.0 out of 10, Exceptional, (31)
"The house was perfect!!! We are a large family coming together from the east coast and west coast. Large bedrooms. Great entertaining space. Communication with owner very easy. I give it 5 stars!!!! "
Historic Country Estate with Fabulous Pool & Pool House!

313 brand new 3 bedroom 2 bath

10.0 out of 10, Exceptional, (1)
"Had some friends in town and needed a place to host everyone, the apartment was clean and spacious and everyone had a great time."
313 brand new 3 bedroom 2 bath

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

10.0 out of 10, Exceptional, (41)
"The house sits high up on the hill with a big deck overlooking the lake. Viewing the lake with coffee in AM, watching the lake activity during day and seeing the moon and lights across the water with a glass of wine at night was lovely. The lake in front of the house is a no wake zone which affords a calmer setting which was really nice. The owner lives in the area and was quickly attentive to answer questions and resolve any small issues that came up. Highly recommend this home."
Entire Private Lakefront Cottage Home on Lake Hopatcong + Kayaks and Pedalboat

Host your family, friends or corporate holidays gatherings here

10.0 out of 10, Exceptional, (10)
"This property was just what we were looking for! The fire pit out back was perfect and easy being gas. It was in a nice area close to where we needed to be. Catalina was super easy to communicate with and got us anything we needed for our stay. We will definitely stay again if we are in the area."
The price is AU$608
includes taxes & fees
3 Feb - 4 Feb
Host your family, friends or corporate holidays gatherings here

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

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

AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC

6.6 out of 10, (4)
"Great room. Awesome house. Maybe upgrade on the towels?"
The price is AU$215
includes taxes & fees
3 Feb - 4 Feb
AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC

Unforgettable sunset view, on the porch…

9.4 out of 10, Exceptional, (45)
"Our stay was very comfortable. We had an incredibly easy check-in and enjoyed the stay."
Unforgettable sunset view, on the porch…

Cheerful 4-Bedroom Lake Home with fire place

9.6 out of 10, Exceptional, (10)
"Great!"
Cheerful 4-Bedroom Lake Home with fire place

213 Brand New 3 Bedroom, 2 Bath, 1 Full Kit, 1 Liv

10.0 out of 10, Exceptional, (1)
"Apartment was clean, spacious and wonderful!"
213 Brand New 3 Bedroom, 2 Bath, 1 Full Kit, 1 Liv

Secluded Cabin w/ Boats < 6 Mi to Jenny Jump!

9.8 out of 10, Exceptional, (24)
"Enjoyed!"
Secluded Cabin w/ Boats < 6 Mi to Jenny Jump!

Main Street Livin’

10.0 out of 10, Exceptional, (48)
"Great home with lots of space and kitchen accessories. Neighborhood was cute though it was quite cold outside! "
Main Street Livin’
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chester you may be interested in

Embassy Suites by Hilton Piscataway Somerset

3.5 star property
8.8 out of 10, Excellent, (1008)
"Very good."
The price is AU$202
includes taxes & fees
10 Feb - 11 Feb
Embassy Suites by Hilton Piscataway Somerset

Sheraton Parsippany Hotel

4.0 star property
8.2 out of 10, Very good, (1004)
"."
The price is AU$234
includes taxes & fees
8 Feb - 9 Feb
Sheraton Parsippany Hotel

Hyatt House Parsippany/Whippany

3.0 star property
8.8 out of 10, Excellent, (1011)
"The only thing make sure the heat is working well specifically in winter time "
The price is AU$212
includes taxes & fees
8 Feb - 9 Feb
Hyatt House Parsippany/Whippany
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.

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, 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?

Stay at beautiful Leisure Lake Lodge: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Chester?

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

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.