Photo by Carrie-Anne Bohn

Chester Holiday Rentals

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Chester holiday rentals

Property grounds
Charming Lake House w/ Large Dock

Holiday Home in Hopatcong

Charming Lake House w/ Large Dock
9.8 out of 10, Exceptional, (8)
"Great stay. Beautiful place "
United States
Joseph M.
The price is HK$573
HK$1,943 total
includes taxes & fees
17 Dec - 18 Dec
Charming Lake House w/ Large Dock
Exterior
Mini Mansion rental suite, close to public transportation, train / buses

Apartment in Plainfield

Mini Mansion rental suite, close to public transportation, train / buses
The price is HK$1,051
HK$1,328 total
includes taxes & fees
21 Dec - 22 Dec
Mini Mansion rental suite, close to public transportation, train / buses
Fridge, microwave, oven, stovetop
Historic Barn View Newton Farm House

Holiday Home in Frelinghuysen Township

Historic Barn View Newton Farm House
10.0 out of 10, Exceptional, (1)
"Was easy to communicate with especially day of when we had some questions "
United States
Lauren L.
The price is HK$934
HK$1,789 total
includes taxes & fees
11 Jan - 12 Jan 2026
Historic Barn View Newton Farm House
Fridge, microwave, oven, stovetop
Cozy Lakeview Cottage minutes from water adventures, farms, wineries, & skiing!

Cottage in Lake Hopatcong

Cozy Lakeview Cottage minutes from water adventures, farms, wineries, & skiing!
9.8 out of 10, Exceptional, (28)
"This cottage was very clean and well organized.The host was very responsive.I would definitely stay here again "
United States
Ken B.
The price is HK$2,140
HK$3,447 total
includes taxes & fees
17 Dec - 18 Dec
Cozy Lakeview Cottage minutes from water adventures, farms, wineries, & skiing!
Microwave, oven, stovetop, dishwasher
Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac

Apartment in Scotch Plains

Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
10.0 out of 10, Exceptional, (1)
"Don was great, very quick with communication and helpful whenever we needed something! The place is in a nice neighborhood with plenty of backyard space. We’re kind of tall people so at times it felt a bit compact but it suited us well for the timing and price. Don provided us with everything to use the fire pit, which we were very excited to do but it was cold and rainy most of the weekend. Would definitely stay again! "
United States
Austin Jared P.
The price is HK$1,167
HK$2,878 total
includes taxes & fees
30 Dec - 31 Dec
Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
Fridge, microwave, oven, stovetop
1bd 1ba Private Apartment Newly Constructed

Apartment in Scotch Plains

1bd 1ba Private Apartment Newly Constructed
2.0 star property
The price is HK$848
HK$1,940 total
includes taxes & fees
17 Dec - 18 Dec
1bd 1ba Private Apartment Newly Constructed
Outdoor dining
Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains

Holiday Home in Scotch Plains

Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
2.0 star property
8.0 out of 10, Very good, (4)
"Very clean, comfortable and safe. Thank you. "
United States
M M.
The price is HK$981
HK$2,119 total
includes taxes & fees
23 Dec - 24 Dec
Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
Exterior
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ

Holiday Home in Hopatcong

Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
9.4 out of 10, Exceptional, (13)
"Flexible and responsive host. Awesome deck overlooking lake."
United States
L T.
The price is HK$1,401
HK$3,947 total
includes taxes & fees
17 Dec - 18 Dec
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
Private kitchen
Country vicinity & Modern Living

Holiday Home in Randolph

Country vicinity & Modern Living
The price is HK$1,098
HK$2,095 total
includes taxes & fees
2 Jan - 3 Jan 2026
Country vicinity & Modern Living
Fridge, stovetop
Town & Country Andover 1st Floor 2 Bedroom

Apartment in Newton

Town & Country Andover 1st Floor 2 Bedroom
The price is HK$849
HK$1,563 total
includes taxes & fees
18 Dec - 19 Dec
Town & Country Andover 1st Floor 2 Bedroom
Property grounds
Cozy Lakefront House with a private dock and lakefront.

Holiday Home in Hopatcong

Cozy Lakefront House with a private dock and lakefront.
9.8 out of 10, Exceptional, (6)
"The home was well appointed and had a beautiful view! Steve was very responsive to all our needs."
United States
Mary Jo Y.
The price is HK$1,440
HK$5,177 total
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy Lakefront House with a private dock and lakefront.
Terrace/patio
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

Holiday Home in Glen Gardner

Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
10.0 out of 10, Exceptional, (33)
"Great communication - beautiful property - highly recommend!"
United States
john w.
The price is HK$19,455
HK$28,499 total
includes taxes & fees
17 Dec - 18 Dec
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
Fridge, microwave, oven, stovetop
Lake Hopatcong Lake House w/Private Dock and Grill

Holiday Home in Lake Hopatcong

Lake Hopatcong Lake House w/Private Dock and Grill
9.8 out of 10, Exceptional, (22)
"Beautiful place. Enjoyed our stay"
United States
William D.
Lake Hopatcong Lake House w/Private Dock and Grill
Exterior
Lakeview House w/ 3 bdrm & 1 bth - newly renovated

Holiday Home in Jefferson

Lakeview House w/ 3 bdrm & 1 bth - newly renovated
2.0 star property
10.0 out of 10, Exceptional, (12)
The price is HK$2,568
HK$4,062 total
includes taxes & fees
17 Dec - 18 Dec
Lakeview House w/ 3 bdrm & 1 bth - newly renovated
Exterior
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)

Apartment in Plainfield

MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
7.6 out of 10, Good, (7)
"It was nice and would be a steal for a few couples combined)."
United States
James
The price is HK$1,576
HK$1,961 total
includes taxes & fees
21 Dec - 22 Dec
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
Terrace/patio
Comfortable, spacious, basement, 1bdrm apartment, sleeps 4

Apartment in Jefferson

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. "
United States
JOSE A
The price is HK$1,513
HK$2,139 total
includes taxes & fees
17 Dec - 18 Dec
Comfortable, spacious, basement, 1bdrm apartment, sleeps 4
1 bedroom, iron/ironing board, WiFi, bed sheets
AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC

Apartment in Plainfield

AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC
5.8 out of 10, (7)
"I had a great time"
United States
joshua M.
The price is HK$700
HK$937 total
includes taxes & fees
19 Dec - 20 Dec
AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC
Private kitchen
Beautiful Lakefront Retreat w/ Deck & Views!

Holiday Home in Newton

Beautiful Lakefront Retreat w/ Deck & Views!
2.0 star property
The price is HK$2,179
HK$6,033 total
includes taxes & fees
23 Dec - 24 Dec
Beautiful Lakefront Retreat w/ Deck & Views!
3 bedrooms, WiFi, bed sheets
3BD 102 Madison Ter S

Holiday Home in Springfield

3BD 102 Madison Ter S
The price is HK$15,564
HK$23,168 total
includes taxes & fees
23 Dec - 24 Dec
3BD 102 Madison Ter S
Stovetop, cookware/dishes/utensils
Town & Country Andover 2nd Floor Area Apartment

Apartment in Andover Township

Town & Country Andover 2nd Floor Area Apartment
2.0 star property
5.6 out of 10, (5)
"Overall good stay at this location. Was there for a wedding and was able to contact the property management clearly and on time. Shopping and amenities nearby and was central to our venue. Would recommend, only complaint if I had one is the heat wouldn't stay on while we were gone for the day but heated up once we set it at night. "
United States
Kalin L.
The price is HK$934
HK$1,703 total
includes taxes & fees
15 Jan - 16 Jan 2026
Town & Country Andover 2nd Floor Area Apartment
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

The Garden Executive Hotel

The Garden Executive Hotel

10/10 Excellent
"Nice"
Christian 1-night trip
Posted 18 hours ago
The Garden Executive Hotel

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?

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.