A stone tower with a metal gate, surrounded by trees and a stone wall.

Cheshire Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Cheshire holiday rentals

A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

1. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AU$294
includes taxes & fees
15 Sept - 16 Sept
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A spacious living area with a sofa, a dining table, and a kitchen in the background.

2. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is AU$634
includes taxes & fees
7 Sept - 8 Sept
#43- Modern Luxury Log Cabin Retreat - Fire Pit
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

3. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AU$411
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private

4. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is AU$406
includes taxes & fees
7 Sept - 8 Sept
All New 1BR with tons of Charm
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

5. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is AU$406
includes taxes & fees
10 Sept - 11 Sept
Newly Remodeled with deck. Close to town center
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

6. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is AU$411
includes taxes & fees
29 Sept - 30 Sept
All New Studio apartment in center of town
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

7. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$406
includes taxes & fees
6 Sept - 7 Sept
Once the old Schools house now a newly furnished Apartment
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

8. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is AU$406
includes taxes & fees
4 Oct - 5 Oct
All New Private and Cozy in great location
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

9. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is AU$406
includes taxes & fees
4 Oct - 5 Oct
All New Fully Furnished Cozy Studio
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

10. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
The price is AU$405
includes taxes & fees
21 Sept - 22 Sept
Brand New Platform #1
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

11. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is AU$882
includes taxes & fees
6 Sept - 7 Sept
The Cottage by the Woods -private getaway to relax
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

12. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AU$541
includes taxes & fees
3 Oct - 4 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

13. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AU$350
includes taxes & fees
7 Sept - 8 Sept
Private Apartment in Southbury 103
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

14. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
Spacious 2 Bedroom apartment close to Yale Bowl
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

15. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is AU$264
includes taxes & fees
30 Sept - 1 Oct
One bedroom in United States of America, New Haven

16. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AU$894
includes taxes & fees
7 Sept - 8 Sept
#41- Available 12/8! - sleeps 14
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

17. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is AU$562
includes taxes & fees
20 Sept - 21 Sept
#24 Serenity A Lakefront Cottage Retreat
A row of brownstone buildings with a central staircase leading to the second floor.

18. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is AU$342
includes taxes & fees
6 Sept - 7 Sept
Bright Downtown Studio near Yale & East Rock!
A loft-style room with a sloped ceiling, a wooden beam, a TV, a white entertainment unit, a black chair, a small table, and a lamp.

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is AU$436
includes taxes & fees
13 Sept - 14 Sept
Bristol Condo Near Espn HQ & Lake Compounce!
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 Cheshire Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"One of the best motels we have stayed in & we have stayed in a lot. Immaculate & excellent value 👏"
Mark 1-night trip
Posted 8 hours ago
Holiday Inn Express Southington by IHG

Find out more about Cheshire

Everything you need to know about Cheshire 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 Cheshire 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 Cheshire holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cheshire holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire 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 Cheshire holiday rentals we have selected for you start as low as AU$324 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire 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 Cheshire 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 Cheshire 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 Cheshire. 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 a holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Barker Character, Comic and Cartoon Museum, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best holiday rentals that Cheshire has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Cheshire is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease 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.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Roaring Brook Park and Drazen Orchards are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Bartlem Park are other places worth a visit.

What’s a holiday rental in Cheshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheshire. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.