Photo by Tai Bui

Cheshire Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Cheshire

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

9.4 out of 10, Exceptional, (8)
"Needed a place to sleep for a couple of nights and this worked for us."
The price is NZ$300
includes taxes & fees
6 Oct - 7 Oct
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (56)
"Loved our stay here. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

Charming Studio| Near Yale| Downtown New Haven

9.2 out of 10, Wonderful, (5)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is NZ$343
includes taxes & fees
6 Oct - 7 Oct
Charming Studio| Near Yale| Downtown New Haven

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (10)
"Great!"
The price is NZ$271
includes taxes & fees
12 Oct - 13 Oct
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Lux Boutique Large Private LOFT Pratt St Hartford

8.4 out of 10, Very good, (21)
"Location was great. Lots of things to do and many nearby options for eating and drinks. View was disappointing—dark and one window facing a brick wall. Biggest complaint was neighbors and noise—first two nights there was loud music and parties until early morning hours."
The price is NZ$279
includes taxes & fees
12 Oct - 13 Oct
Lux Boutique Large Private LOFT Pratt St Hartford

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (25)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
The price is NZ$299
includes taxes & fees
6 Oct - 7 Oct
Cozy apartment in charming Hartford with AC, WiFi

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
The price is NZ$542
includes taxes & fees
6 Oct - 7 Oct
Private Apartment in Berlin

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

7.0 out of 10, Good, (2)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
The price is NZ$482
includes taxes & fees
13 Oct - 14 Oct
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

Conference Room Rental no sleeping arrangements

The price is NZ$1,592
includes taxes & fees
6 Oct - 7 Oct
Conference Room Rental no sleeping arrangements

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (7)
"My best friend and I wanted to get out of the city with our pups for a long weekend, and this was absolutely the perfect place to do that! Robert was accommodating, kind, and quick to respond. And the neighborhood/community is adorable, friendly, and low key. Being literally steps from the beach was beyond amazing, and being able to sit on the front patio and get the breeze/view was unmatched! Can’t wait to come back again! "
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Stunning Apt W/ Parking and Gym | Downtown at Yale

10.0 out of 10, Exceptional, (44)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
Stunning Apt W/ Parking and Gym | Downtown at Yale

New Cozy 2BR Stay New Haven Close to Yale

2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
The price is NZ$438
includes taxes & fees
12 Oct - 13 Oct
New Cozy 2BR Stay New Haven Close to Yale

Cozy Safe Home

The price is NZ$619
includes taxes & fees
6 Oct - 7 Oct
Cozy Safe Home

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

9.6 out of 10, Exceptional, (4)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
The price is NZ$345
includes taxes & fees
1 Nov - 2 Nov
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
The price is NZ$429
includes taxes & fees
6 Oct - 7 Oct
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
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 Cheshire Hotel Reviews

Find out more about Cheshire

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 favorite 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 depends 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 NZ$271 per night. Entering your travel dates in the search wizard you might find 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?

Private Apartment in Berlin: This holiday home rental outside of Cheshire is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.