Cheshire Holiday Rentals

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Our top choices for Cheshire holiday rentals

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
8.0 out of 10, Very good, (1 review)
"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$639
includes taxes & fees
9 June - 10 June
#43- Modern Luxury Log Cabin Retreat | Fire Pit

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is AU$300
includes taxes & fees
7 June - 8 June
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is AU$414
includes taxes & fees
8 June - 9 June
2BR Apartment Near Wesleyan 102

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$413
includes taxes & fees
11 June - 12 June
Once the old Schools house now a newly furnished Apartment

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is AU$529
includes taxes & fees
16 June - 17 June
#24 *Serenity* A Lakefront Cottage Retreat

Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Mill River
10.0 out of 10, Exceptional, (2 reviews)
"This apartment in a 4 unit building with its own parking lot was on a quiet street. Easy to get to no matter what side of the city I came from and close enough to walk to downtown (6 blocks) and half a block off the famous Little Italy street for food and cocktails and then brunch and coffee in walking distance in the mornings too. The unit had everything you need, fully stocked kitchen and bath, shared laundry. Great mattress and pillows! Easy keypad entry. I’d stay there over and over again!"
United States
Erica S.
The price is AU$440
includes taxes & fees
8 June - 9 June
Cozy Stay by Little Italy & Wooster Street

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is AU$489
includes taxes & fees
9 June - 10 June
Angelica’s safe haven @ west haven

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (15 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveller
The price is AU$401
includes taxes & fees
10 June - 11 June
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (1 review)
"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$256
includes taxes & fees
8 June - 9 June
One bedroom in United States of America, New Haven

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
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$326
includes taxes & fees
21 June - 22 June
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is AU$330
includes taxes & fees
26 June - 27 June
Modern Studio Retreat

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, (73 reviews)
"Spacious"
United States
Mehul
The price is AU$324
includes taxes & fees
7 June - 8 June
Spacious 2 Bedroom apartment close to Yale Bowl

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (30 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is AU$176
includes taxes & fees
9 June - 10 June
Cozy One Bedroom Apartment Centrally Located in Southbury

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is AU$355
includes taxes & fees
7 June - 8 June
Spacious Bohemian Nook

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (31 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is AU$409
includes taxes & fees
23 June - 24 June
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is AU$449
includes taxes & fees
7 June - 8 June
1 Min to I-91 - Newly Renovated Modern 2 BR Home

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Host had great communication. The unit was clean, cozy and comfortable. Will book again when in the area."
United States
Tod B.
The price is AU$354
includes taxes & fees
7 June - 8 June
The Sun Filled Cozy Creamery

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (10 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$413
includes taxes & fees
6 June - 7 June
All New 1BR with tons of Charm

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is AU$413
includes taxes & fees
7 June - 8 June
All new 1BR apartment with all the features you are looking for

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is AU$507
includes taxes & fees
8 June - 9 June
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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 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 Cheshire Hollow Farm, 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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: 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 Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, 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.