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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester holiday rentals

1. Secluded 6BR Retreat Near Lake Hopatcong

Secluded 6BR Retreat Near Lake Hopatcong
Roxbury Township
The price is NZ$935
includes taxes & fees
5 Aug - 6 Aug
Secluded 6BR Retreat Near Lake Hopatcong

2. 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 NZ$621
includes taxes & fees
5 Aug - 6 Aug
Lee's House - Lakeview House w/ 3 bdrm & 1 bth

3. 1BR Rustic-Chic Barn Getaway with Private Fire Pit

1BR Rustic-Chic Barn Getaway with Private Fire Pit
Byram Township
The price is NZ$488
includes taxes & fees
1 Sept - 2 Sept
1BR Rustic-Chic Barn Getaway with Private Fire Pit

4. Lakeview Cottage Near Restaurants & Wedding Venues

Lakeview Cottage Near Restaurants & Wedding Venues
Lake Hopatcong
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Jenna was a wonderful host—very responsive and helpful. Everything was smooth and stress-free. Would definitely stay again!"
United States
Bana S.
The price is NZ$645
includes taxes & fees
9 Aug - 10 Aug
Lakeview Cottage Near Restaurants & Wedding Venues

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

Stylish & Modern Entire Private Suite - near NYC / minutes to Morristown
Boonton
The price is NZ$398
includes taxes & fees
31 Aug - 1 Sept
Stylish & Modern Entire Private Suite - near NYC / minutes to Morristown

6. Pet-Friendly Home w/ Lake Views & Deck!

Pet-Friendly Home w/ Lake Views & Deck!
Stanhope
8.0 out of 10, Very good, (2 reviews)
"SUPER Clean, well-laid out, and just as advertised! The hosts were great, the check-in could not have been easier. We loved this place, even though it was only for one weekend."
United States
Brendan Q.
The price is NZ$810
includes taxes & fees
16 Aug - 17 Aug
Pet-Friendly Home w/ Lake Views & Deck!

7. Pet-friendly Home w/ Lake Views & Deck!

Pet-friendly Home w/ Lake Views & Deck!
3.0 star property
Stanhope
The price is NZ$803
includes taxes & fees
5 Aug - 6 Aug
Pet-friendly Home w/ Lake Views & Deck!

8. 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 NZ$352
includes taxes & fees
2 Sept - 3 Sept
Historic Barn View Newton Farm House Unit

9. 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 NZ$205
includes taxes & fees
5 Aug - 6 Aug
AFFORDABLE SUITE IN MINI MANION NEAR PUBLIC TRANSPORTATION AND SHOPPING DISTRIC

10. 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 NZ$510
includes taxes & fees
6 Aug - 7 Aug
Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains

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

Mini Mansion rental suite, close to public transportation, train / buses
Plainfield
The price is NZ$290
includes taxes & fees
9 Aug - 10 Aug
Mini Mansion rental suite, close to public transportation, train / buses

12. 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, (9 reviews)
"Place was great and very neat, home setting, had everything we needed. Great place"
United States
Alicia P.
The price is NZ$425
includes taxes & fees
3 Sept - 4 Sept
Private and Cozy 2 Bedroom House with Amenities!

13. 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 NZ$700
includes taxes & fees
5 Aug - 6 Aug
Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac

14. 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 NZ$452
includes taxes & fees
26 Aug - 27 Aug
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC

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 NZ$573
includes taxes & fees
31 Aug - 1 Sept
Private 1BR Apt, 2BD 1BA, Sleeps 5, Clean & Reliable, Near NYC

16. 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 NZ$1,575
includes taxes & fees
1 Sept - 2 Sept
Cozy Lakefront House with a private dock and lakefront.

17. 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 NZ$329
includes taxes & fees
10 Aug - 11 Aug
Town & Country Andover, NJ Area Apt- 2nd Fl

18. 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 NZ$226
includes taxes & fees
2 Sept - 3 Sept
Town & Country Andover, NJ Area- Studio Unit

19. Luxury 2BR Home | 2.5 Baths & Modern Comfort

Luxury 2BR Home | 2.5 Baths & Modern Comfort
Caldwell
The price is NZ$883
includes taxes & fees
5 Aug - 6 Aug
Luxury 2BR Home | 2.5 Baths & Modern Comfort

20. 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 NZ$425
includes taxes & fees
5 Aug - 6 Aug
MINI MANSION WHOLE RIGHT WING, THREE BEDROOM APARTMENT AVAILABLE AT A (LOW RATE)
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

Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as NZ$329 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Entire Private Lakefront Home on Lake Hopatcong + Kayaks and Pedalboat, 3Bd,1bth: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

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.