Cheshire Holiday Rentals

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Our top choices for Cheshire holiday rentals

9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is AU$286
includes taxes & fees
30 Mar - 31 Mar
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$432
includes taxes & fees
7 Mar - 8 Mar
Once the old Schools house now a newly furnished Apartment

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AU$305
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is AU$364
includes taxes & fees
12 Mar - 13 Mar
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is AU$489
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is AU$492
includes taxes & fees
7 Mar - 8 Mar
Angelica’s safe haven @ west haven

Apartment in Wallingford Center

All New Studio apartment in center of town
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$452
includes taxes & fees
7 Mar - 8 Mar
All New Studio apartment in center of town

Apartment in Dwight

Downtown New Haven Escape
8.0 out of 10, Very good, (6 reviews)
"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."
United States
Michael H.
The price is AU$343
includes taxes & fees
7 Mar - 8 Mar
Downtown New Haven Escape

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$432
includes taxes & fees
8 Mar - 9 Mar
All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (7 reviews)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is AU$722
includes taxes & fees
16 Mar - 17 Mar
The Jewel of The Cove - Historic Coastal Retreat
8.0 out of 10, Very good, (2 reviews)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is AU$330
includes taxes & fees
7 Mar - 8 Mar
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is AU$456
includes taxes & fees
9 Mar - 10 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is AU$597
includes taxes & fees
8 Mar - 9 Mar
Cozy & Serene Cabin with Fireplace, Ski Nearby!
10.0 out of 10, Exceptional, (1 review)
"Super great communication and help getting situated in the room!"
United States
Glenn
The price is AU$221
includes taxes & fees
9 Mar - 10 Mar
Cozy Room in charming New Haven near Yale/Hospitals!

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (10 reviews)
"Had a great stay!"
United States
Jeffrey C.
The price is AU$291
includes taxes & fees
7 Mar - 8 Mar
Yale Casa Verde Studio
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is AU$322
includes taxes & fees
9 Mar - 10 Mar
Stocked home close to Yale, in Heart of New Haven
9.6 out of 10, Exceptional, (69 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is AU$327
includes taxes & fees
20 Mar - 21 Mar
Spacious 2 Bedroom apartment close to Yale Bowl
9.8 out of 10, Exceptional, (14 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is AU$496
includes taxes & fees
14 Mar - 15 Mar
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is AU$349
includes taxes & fees
9 Mar - 10 Mar
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Holiday Home in West Haven

McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is AU$743
includes taxes & fees
8 Mar - 9 Mar
McAngel Haven: 5 mins from Yale
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

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$278 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?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: This holiday home rental outside of Cheshire is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

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 Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Drazen Orchards 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.