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

Chester Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chester holiday rentals

Property grounds

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

1BR Rustic-Chic Barn Getaway with Private Fire Pit
Byram Township
The price is HK$881
HK$2,387 total
includes taxes & fees
23 Aug - 24 Aug
1BR Rustic-Chic Barn Getaway with Private Fire Pit
Property grounds

2. 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$1,746
HK$4,225 total
includes taxes & fees
25 Aug - 26 Aug
Luxury 2BR Lakefront w/ Dock & Kayaks
Exterior

3. 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, (14 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$2,148
HK$3,623 total
includes taxes & fees
21 Sept - 22 Sept
Lee's House - Lakeview House w/ 3 bdrm & 1 bth
Exterior

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$4,299 total
includes taxes & fees
20 Sept - 21 Sept
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
Private kitchen

5. Lakeview Cottage Near Restaurants & Wedding Venues

Lakeview Cottage Near Restaurants & Wedding Venues
Lake Hopatcong
9.8 out of 10, Exceptional, (30 reviews)
"The property is close to everything on the lake. Everything about our stay was smoothly done and top notch."
United States
Mark
The price is HK$2,114
HK$3,447 total
includes taxes & fees
31 Aug - 1 Sept
Lakeview Cottage Near Restaurants & Wedding Venues
Room

6. Stylish & Modern Entire Private Suite - near NYC / minutes to Morristown

Stylish & Modern Entire Private Suite - near NYC / minutes to Morristown
Boonton
The price is HK$967
HK$2,007 total
includes taxes & fees
7 Sept - 8 Sept
Stylish & Modern Entire Private Suite - near NYC / minutes to Morristown
Exterior

7. Historic Barn View | Cozy Ground Level Retreat

Historic Barn View | Cozy Ground Level Retreat
Frelinghuysen Township
The price is HK$1,090
HK$1,531 total
includes taxes & fees
2 Sept - 3 Sept
Historic Barn View | Cozy Ground Level Retreat
Interior

8. AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC

AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC
Plainfield
5.8 out of 10, (7 reviews)
"I had a great time"
United States
joshua M.
The price is HK$706
HK$944 total
includes taxes & fees
24 Aug - 25 Aug
AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC
Exterior

9. 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$1,058
HK$1,338 total
includes taxes & fees
24 Aug - 25 Aug
Mini Mansion rental suite, close to public transportation, train / buses
Property grounds

10. 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$2,611
HK$6,899 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Lakefront House with a private dock and lakefront.
Living area

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

Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
Scotch Plains
The price is HK$873
HK$2,132 total
includes taxes & fees
31 Aug - 1 Sept
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
Private kitchen

12. Convenient 3 Bed/1 Bath Home

Convenient 3 Bed/1 Bath Home
Livingston
The price is HK$1,325
HK$3,233 total
includes taxes & fees
17 Sept - 18 Sept
Convenient 3 Bed/1 Bath Home
Private kitchen

13. 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$1,060
HK$2,412 total
includes taxes & fees
31 Aug - 1 Sept
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC
Living area

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

Town & Country Andover, NJ Area Apt- 2nd Fl
Andover Township
6.4 out of 10, (6 reviews)
"Great host! Very nice apartment with everything you could need. "
United States
Madison P.
The price is HK$1,176
HK$1,623 total
includes taxes & fees
31 Aug - 1 Sept
Town & Country Andover, NJ Area Apt- 2nd Fl
Interior

15. Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains

Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
Scotch Plains
9.0 out of 10, Wonderful, (9 reviews)
"Owner lives upstairs and is very kind and respectful. We had absolutely no issues. "
United States
Samantha H.
The price is HK$1,098
HK$2,375 total
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
Exterior

16. 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$1,411
HK$3,257 total
includes taxes & fees
22 Aug - 23 Aug
Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
Room

17. Town & Country Andover, NJ Area- Studio Unit

Town & Country Andover, NJ Area- Studio Unit
Newton
3.0 out of 10, (2 reviews)
"We came for 1 night on a weeknight, the room itself was fine but the next door neighbors (shared wall) were extremely loud (shouting after midnight) and smoking weed, which made our room smell. Would not recommend "
United States
Tyler M.
The price is HK$682
HK$1,043 total
includes taxes & fees
1 Sept - 2 Sept
Town & Country Andover, NJ Area- Studio Unit
Interior

18. Private Waterfront Home Nestled In A Quiet Section Of Lake Hopatcong

Private Waterfront Home Nestled In A Quiet Section Of Lake Hopatcong
Jefferson
8.6 out of 10, Excellent, (4 reviews)
"Nice place"
United States
Peter T.
The price is HK$2,494
HK$5,211 total
includes taxes & fees
30 Aug - 31 Aug
Private Waterfront Home Nestled In A Quiet Section Of Lake Hopatcong
Living area

19. Private and Cozy 2 Bedroom House with Amenities!

Private and Cozy 2 Bedroom House with Amenities!
Union Township
8.6 out of 10, Excellent, (11 reviews)
"Place was great and very neat, home setting, had everything we needed. Great place"
United States
Alicia P.
The price is HK$1,192
HK$1,995 total
includes taxes & fees
3 Sept - 4 Sept
Private and Cozy 2 Bedroom House with Amenities!
Interior

20. Madison Home w/ Patio: Walk to Main Street!

Madison Home w/ Patio: Walk to Main Street!
3.0 star property
Madison
6.0 out of 10, (1 review)
"You only learned after booking that the owner would be in the basement at all times and moving cars around constantly. That was not explained in the listing. He also mowed the lawn while we were there, which was not pleasant while trying to nap. The keypad to enter the home doesn’t work properly and you have to type the code multiple times to finally enter. The beds are not comfortable at all. With the price of this location, the beds should be worth the price. The window fans do not keep the...
United States
Anonymous traveller
The price is HK$2,141
HK$4,200 total
includes taxes & fees
8 Sept - 9 Sept
Madison Home w/ Patio: Walk to Main Street!
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

Hotel Troy, Trademark Collection by Wyndham

Hotel Troy, Trademark Collection by Wyndham

10/10 Excellent
"This hotel is beautiful , clean and staff was very helpful. We didn’t realize it caters to business travelers (which is totally fine- I can see why they would want to stay there with all the meeting spaces and cubbies). The only issue we had was with the shower- the glass panel only covers half the shower so water gets all over the floor. Nice design aesthetically but not practical. Otherwise our stay was perfect!"
Elissa 2-night trip
Posted 16 hours ago
Hotel Troy, Trademark Collection by Wyndham

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.