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, (27)
"Had everything we needed. Enjoyred our stay very much. Easy access to NYC. Everyone had fun. 3 floors is great. "
The price is AU$2,888
includes taxes & fees
1 July - 2 July
1897 MANSION 30 min to NYC Sleeps up to 26 with 12 bedrooms and 7 and 1/2 baths

BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom

9.4 out of 10, Exceptional, (14)
"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 AU$1,283
includes taxes & fees
10 June - 11 June
BestOBothWorlds.2G@HandcraftedWoodTerrace.GameRoom

New Modern Ranch Close to it All

5.4 out of 10, (3)
"Well-maintainedNice amenities"
New Modern Ranch Close to it All

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 AU$5,132
includes taxes & fees
10 June - 11 June
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

Unforgettable sunset view, on the porch…

9.2 out of 10, Wonderful, (47)
"Our stay was very comfortable. We had an incredibly easy check-in and enjoyed the stay."
Unforgettable sunset view, on the porch…

4 Bedroom Lake Hopatcong Lakehouse with Kayaks and Paddleboat

10.0 out of 10, Exceptional, (12)
"Perfect for what we needed"
4 Bedroom Lake Hopatcong Lakehouse with Kayaks and Paddleboat

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

9.8 out of 10, Exceptional, (6)
"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

Lake house

8.0 out of 10, Very good, (2)
"We are old people and it was a big problem for us unpack our staff, we also was very upset about fireplace it was no fireplace Everything else was great especially sauna my favorite place we are having a very good time with our friends Thank you very much for having us Leszek "
The price is AU$1,015
includes taxes & fees
16 June - 17 June
Lake house

Total privacy and relaxation in a secluded 3 bed/ 2 bath house on 5 acres.

10.0 out of 10, Exceptional, (33)
"Great place to stay. Close to downtown…"
Total privacy and relaxation in a secluded 3 bed/ 2 bath house on 5 acres.

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

Charming Apartment in Flemington

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

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

9.8 out of 10, Exceptional, (25)
"Awesome place to stay. Everyone enjoyed to the max. Place to take your family for a great stay"
Secluded Cabin w/ Boats < 6 Mi to Jenny Jump!

Madison Home: Walk to Main Street!

2.0 star property
8.8 out of 10, Excellent, (13)
"We had a wonderful stay at this property. House was clean and had what we needed for our family of 4. And the host was very welcoming and reachable. "
Madison Home: Walk to Main Street!

Luxury Log Cabin w/ EV Charger & Mtn Views!

9.8 out of 10, Exceptional, (9)
"We enjoyed the house. The kitchen was very nicely equipped. "
Luxury Log Cabin w/ EV Charger & Mtn Views!

Cozy Cabin with Hot Tub, Private Lake & Game Room

9.4 out of 10, Exceptional, (13)
"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

Stay at beautiful Leisure Lake Lodge

10.0 out of 10, Exceptional, (128)
"Very Beautiful lake house. We all enjoyed with family. Bob is a very good host.Will definitely come again. "
Stay at beautiful Leisure Lake Lodge

LUXURIOUS RETREAT IN A TRANQUIL SMALL TOWN FOR A PEACEFUL GETAWAY

2.0 out of 10, (2)
"Unfortunately this rental does not exist. My family and I had to find a place to stay on our own 3 days before my nieces wedding. Very unfair situation."
LUXURIOUS RETREAT IN A TRANQUIL SMALL TOWN FOR A PEACEFUL GETAWAY

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

9.4 out of 10, Exceptional, (6)
"Very comfortable with great views. It was cold outside but toasty and warm inside. Had everything we needed."
The price is AU$685
includes taxes & fees
10 June - 11 June
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ

Main Street Livin’

10.0 out of 10, Exceptional, (50)
"Great place"
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.
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?

Lake house: This holiday home rental outside of Chester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

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.