A stone waterfall in a forested area with a stone wall in the background.

Chester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chester holiday rentals

A dock with chairs and a table by a lake, a small building on the water, and a forested hill in the background.

1. Luxury 2BR Lakefront w/ Dock & Kayaks

Luxury 2BR Lakefront w/ Dock & Kayaks
Hopatcong
9.6 out of 10, Exceptional, (15 reviews)
"Great view and stay."
United States
Byunghyun A.
The price is HK$979
HK$3,198 total
includes taxes & fees
7 Oct - 8 Oct
Luxury 2BR Lakefront w/ Dock & Kayaks
A wooden deck with a railing, leading to a building with a window and a door.

2. Secluded 6BR Retreat Near Lake Hopatcong

Secluded 6BR Retreat Near Lake Hopatcong
Roxbury Township
The price is HK$2,930
HK$6,107 total
includes taxes & fees
11 Oct - 12 Oct
Secluded 6BR Retreat Near Lake Hopatcong
A dining area with a long table, multiple chairs, a television displaying a fireplace, and a modern ceiling light fixture.

3. Lux Lakeview Experience Sleep 8

Lux Lakeview Experience Sleep 8
Hopatcong
Lux Lakeview Experience Sleep 8
A dock with a Yamaha boat, a stone retaining wall, and a blue house with a balcony.

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

Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
Hopatcong
9.4 out of 10, Exceptional, (14 reviews)
"Great host and location. Easy to find and easy to park!"
United States
Daniel S.
The price is HK$1,569
HK$4,246 total
includes taxes & fees
13 Oct - 14 Oct
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
A wooden deck with a table and chairs, overlooking a lake with houses in the background.

5. Cozy Lakefront House with a private dock and lakefront.

Cozy Lakefront House with a private dock and lakefront.
Hopatcong
9.8 out of 10, Exceptional, (7 reviews)
"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$1,569
HK$5,496 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Lakefront House with a private dock and lakefront.
A waterfront building with a sign reading 'The Windlass,' featuring a row of wooden paddle boats.

6. Lee's House - Lakeview House w/ 3 bdrm & 1 bth

Lee's House - Lakeview House w/ 3 bdrm & 1 bth
Jefferson
10.0 out of 10, Exceptional, (18 reviews)
"Everything was well stocked, plenty of space, short walk to a nice restaurant and very comfortable. Would definitely stay again!"
United States
Deidre R.
The price is HK$1,847
HK$3,236 total
includes taxes & fees
2 Nov - 3 Nov
Lee's House - Lakeview House w/ 3 bdrm & 1 bth
A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

7. BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom

BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom
Jefferson
9.2 out of 10, Wonderful, (20 reviews)
"Very attentive hosts. Great location."
United States
Gwen V.
The price is HK$4,645
HK$7,730 total
includes taxes & fees
10 Oct - 11 Oct
BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom
A rustic outdoor setting with a fire pit, benches, and a small shed.

8. 1BR Rustic-Chic Barn Getaway with Private Fire Pit

1BR Rustic-Chic Barn Getaway with Private Fire Pit
Byram Township
8.0 out of 10, Very good, (2 reviews)
"Everything was exactly as described in the listing. It had everything we needed for our quick trip. Plenty of room for the two of us and our small dogs. There are a couple of nice grass areas to walk them around. And we found several nice trails to walk not too far away. Communication with the host was excellent and always very responsive. The check in and out process was simple. We are very satisfied and would definitely stay here again if we make it back this way someday."
United States
Ashley G.
The price is HK$645
HK$2,070 total
includes taxes & fees
13 Oct - 14 Oct
1BR Rustic-Chic Barn Getaway with Private Fire Pit
Living Room (2)

9. Historic Barn View Newton Farm House Unit

Historic Barn View Newton Farm House Unit
Frelinghuysen Township
10.0 out of 10, Exceptional, (2 reviews)
"Was easy to communicate with especially day of when we had some questions "
United States
Lauren L.
The price is HK$1,012
HK$1,433 total
includes taxes & fees
12 Oct - 13 Oct
Historic Barn View Newton Farm House Unit
Living Room (1)

10. Town & Country Andover, NJ Area Apt- 2nd Fl

Town & Country Andover, NJ Area Apt- 2nd Fl
Andover Township
7.0 out of 10, Good, (7 reviews)
"Great host! Very nice apartment with everything you could need. "
United States
Madison P.
The price is HK$1,012
HK$1,426 total
includes taxes & fees
7 Oct - 8 Oct
Town & Country Andover, NJ Area Apt- 2nd Fl
A two-story house with a balcony, a covered deck, and a dock extending into the water.

11. Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner

Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner
Jefferson
10.0 out of 10, Exceptional, (4 reviews)
"Owner Lori is a wonderful and caring host!Beautiful and charming home on the lake. Clean and comfortable accommodations with lovely views. Looking forward to a return trip!"
United States
Ann D.
The price is HK$3,094
HK$5,949 total
includes taxes & fees
19 Oct - 20 Oct
Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

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

MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
Plainfield
7.6 out of 10, Good, (7 reviews)
"It was nice and would be a steal for a few couples combined)."
United States
James
The price is HK$1,589
HK$1,978 total
includes taxes & fees
12 Oct - 13 Oct
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
Entrance overview

13. Town & Country Andover NJ Area Apt -1st Fl

Town & Country Andover NJ Area Apt -1st Fl
Newton
The price is HK$942
HK$1,344 total
includes taxes & fees
13 Oct - 14 Oct
Town & Country Andover NJ Area Apt -1st Fl
A dining area with a round wooden table, two chairs, a framed picture, and a wall-mounted light fixture.

14. Isaac Read Cottage—Historic Hope property near DWG

Isaac Read Cottage—Historic Hope property near DWG
Blairstown
The price is HK$1,271
HK$2,376 total
includes taxes & fees
7 Oct - 8 Oct
Isaac Read Cottage—Historic Hope property near DWG
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dining area with a round table and two chairs.

15. Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC

Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
Scotch Plains
10.0 out of 10, Exceptional, (4 reviews)
"Really nice place and perfect spot for us visiting family in Cranford, Fanwood and Elizabeth."
United States
Tim B.
The price is HK$1,127
HK$2,488 total
includes taxes & fees
10 Oct - 11 Oct
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
A modern apartment with a kitchen, dining area, and living room.

16. Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC

Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
Scotch Plains
10.0 out of 10, Exceptional, (1 review)
"Great location, nice and clean, exactly like the pictures."
United States
Frederic K.
The price is HK$1,123
HK$2,483 total
includes taxes & fees
11 Oct - 12 Oct
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
A hotel reception desk with a sign that reads 'We'll leave the light on for you.'

17. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Piscataway
10.0 out of 10, Exceptional, (3 reviews)
"Affordable spot with solid WiFi and private bathroom. Exactly what I wanted for the price."
United States
Anonymous traveller
The price is HK$678
HK$778 total
includes taxes & fees
18 Oct - 19 Oct
1 King Bed | Non-Smoking
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

18. Mini Mansion rental suite, close to public transportation, train / buses

Mini Mansion rental suite, close to public transportation, train / buses
Plainfield
The price is HK$1,059
HK$1,339 total
includes taxes & fees
7 Oct - 8 Oct
Mini Mansion rental suite, close to public transportation, train / buses
A spacious living area with a sofa, a coffee table, and a patterned rug. A staircase leads to an upper floor, and a kitchen area is visible in the background.

19. Private and Cozy 2 Bedroom House with Amenities!

Private and Cozy 2 Bedroom House with Amenities!
Union Township
8.4 out of 10, Very good, (16 reviews)
"Place was great and very neat, home setting, had everything we needed. Great place"
United States
Alicia P.
The price is HK$1,095
HK$1,856 total
includes taxes & fees
7 Oct - 8 Oct
Private and Cozy 2 Bedroom House with Amenities!
A small, single-story shed with a white door and windows, surrounded by a white picket fence and potted plants.

20. Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac

Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
Scotch Plains
10.0 out of 10, Exceptional, (3 reviews)
"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$1,412
HK$3,259 total
includes taxes & fees
1 Nov - 2 Nov
Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
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

Madison Hotel

Madison Hotel

10/10 Excellent
"Lively, breakfast included."
Lourdes 6-night trip
Posted 7 hours ago
Madison 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?

New Modern Ranch Close to it All: This holiday home rental outside of Chester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.