Photo by Kristin Patton

Chester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Chester

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

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"We loved our stay. The location was perfect to visit family, the house was clean, bright, with a lot of windows, and close to shopping. The yard is amazing (park-like), and very relaxing to just sit and look at. We'll be back the next time we visit NJ."
Charming 2-bedroom house on 2 dog friendly landscaped acres in lovely Chester
New Modern Ranch Close to it All
3 bedrooms, iron/ironing board, WiFi, bed sheets

New Modern Ranch Close to it All

6.6 out of 10, (4)
"Well-maintainedNice amenities"
New Modern Ranch Close to it All
Stay at beautiful Leisure Lake Lodge
Terrace/patio

Stay at beautiful Leisure Lake Lodge

10.0 out of 10, Exceptional, (129)
"This was a wonderful place to visit with family. It was well stocked and very comfortable and just beautiful. Planning to come back again this fall. Only problem was the many steps down to the house. We did okay but could be difficult for anyone who can’t do stairs. "
Stay at beautiful Leisure Lake Lodge
1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths
Interior

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, (33)
"The house was great, everyone was very accommodating! "
The price is HK$6,939
HK$14,473 total
includes taxes & fees
20 Oct - 21 Oct
1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths
Historic 5-bedroom house with beautiful back yard suitable for private events.
Outdoor dining

Historic 5-bedroom house with beautiful back yard suitable for private events.

The price is HK$3,112
HK$3,855 total
includes taxes & fees
3 Oct - 4 Oct
Historic 5-bedroom house with beautiful back yard suitable for private events.
New Cozy pristine home in Mountainside NJ, Mins to NYC free coffee, Smart Tvs +
3 bedrooms, iron/ironing board, WiFi, bed sheets

New Cozy pristine home in Mountainside NJ, Mins to NYC free coffee, Smart Tvs +

10.0 out of 10, Exceptional, (1)
"Clean, spacious, and well equipped. We had a great stay."
New Cozy pristine home in Mountainside NJ, Mins to NYC free coffee, Smart Tvs +
Home Away From Home -- with pools, parks, hiking, fishing, and lakes nearby!
Fridge, microwave, stovetop, coffee/tea maker

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 HK$2,062
HK$3,559 total
includes taxes & fees
30 Oct - 31 Oct
Home Away From Home -- with pools, parks, hiking, fishing, and lakes nearby!
Unforgettable sunset view, on the porch…
Exterior

Unforgettable sunset view, on the porch…

9.2 out of 10, Wonderful, (54)
"Excellent stay, great host & very clean place! Thank you!"
Unforgettable sunset view, on the porch…
Cheerful Cottage with hot tub
Outdoor spa tub

Cheerful Cottage with hot tub

10.0 out of 10, Exceptional, (16)
"Rented cottage for Christmas time, my family and I had such a nice time! Super clean and great location and views of lake! "
Cheerful Cottage with hot tub
Charming 2-bedroom apartment with WiFi, AC in tranquil Morristown
Outdoor dining

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

8.8 out of 10, Excellent, (10)
"Perfect location beautiful bedrooms lovely host "
Charming 2-bedroom apartment with WiFi, AC in tranquil Morristown
Historic Country Estate with Fabulous Pool & Pool House!
Outdoor pool, a heated pool

Historic Country Estate with Fabulous Pool & Pool House!

10.0 out of 10, Exceptional, (39)
"We had an incredible time on our family reunion at Jeff's house. The house is incredible, stocked, and exactly like the pics if not even better. Great location to go out or bring in food. Will definitely come back!"
Historic Country Estate with Fabulous Pool & Pool House!
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
Exterior

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 HK$1,575
HK$1,984 total
includes taxes & fees
1 Oct - 2 Oct
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
Terrace/patio

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 HK$19,449
HK$28,047 total
includes taxes & fees
30 Sept - 1 Oct
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
Elegant & Private Sparta Home – Pool, Deck, and Luxury Comfort
Property grounds

Elegant & Private Sparta Home – Pool, Deck, and Luxury Comfort

10.0 out of 10, Exceptional, (19)
"Absolutely stunning home and property! We can’t find one negative thing to say about our stay. It was a pleasure to dealing withthe owners. They were accommodating, prompt in responding and overall amazing. We simply did not want to leave. Everything was wonderful, EXTREMELY clean, quiet, relaxing and beautiful. I wish I took more pictures but we didn’t to disconnect from our electronics and phones to enjoy quality time as a family and this house made it easy to do!! We can’t recommend this...
Elegant & Private Sparta Home – Pool, Deck, and Luxury Comfort
Stay at Chalet 11, 22
TV, fireplace, ping pong

Stay at Chalet 11, 22

10.0 out of 10, Exceptional, (1)
"Really nice stay at this property - hosts were responsive, and left everything in great condition for us. Definitely a spot we'd love to use again. "
The price is HK$8,192
HK$12,471 total
includes taxes & fees
30 Sept - 1 Oct
Stay at Chalet 11, 22
Comfortable, spacious, basement, 1bdrm apartment, sleeps 4
Terrace/patio

Comfortable, spacious, basement, 1bdrm apartment, sleeps 4

10.0 out of 10, Exceptional, (1)
"It is a gorgeous space with everything that you may need for a beautiful stay. The apartment is very organized, clean and welcoming. The back yard is absolutely amazing in nature. The house has a pool which you can use with prior authorization from the owner. The host/owner is very polite and resourceful. We will be coming back. "
The price is HK$1,512
HK$2,123 total
includes taxes & fees
1 Oct - 2 Oct
Comfortable, spacious, basement, 1bdrm apartment, sleeps 4
Cozy large space with private Sauna, gym & office in a tranquil neighborhood
Fridge, microwave, oven, dishwasher

Cozy large space with private Sauna, gym & office in a tranquil neighborhood

Cozy large space with private Sauna, gym & office in a tranquil neighborhood
Peaceful LakeHouse w/ Spa, Lake Views/Access, and Game Room
Terrace/patio

Peaceful LakeHouse w/ Spa, Lake Views/Access, and Game Room

8.0 out of 10, Very good, (6)
"Good place and a nice time."
Peaceful LakeHouse w/ Spa, Lake Views/Access, and Game Room
BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom
Beach nearby, sun-loungers, beach towels

BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom

9.4 out of 10, Exceptional, (16)
"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 HK$4,397
HK$7,408 total
includes taxes & fees
13 Oct - 14 Oct
BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom
4 Bedroom Lake Hopatcong Lakehouse with Kayaks and Paddleboat
Outdoor dining

4 Bedroom Lake Hopatcong Lakehouse with Kayaks and Paddleboat

10.0 out of 10, Exceptional, (15)
"We had a great stay. We were mainly in town for a conference and just needed a place to gather at night. It was just what we needed."
4 Bedroom Lake Hopatcong Lakehouse with Kayaks and Paddleboat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Embassy Suites by Hilton Berkeley Heights

Embassy Suites by Hilton Berkeley Heights

10/10 Excellent
"Both great"
Daniel 1-night trip
Posted 17 hours ago
Embassy Suites by Hilton Berkeley Heights

Find out more about Chester

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Private and Cozy 2 Bedroom House with Amenities!: This holiday home rental outside of Chester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as an oven and a microwave can make your holiday run smoothly.

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.