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

Cheshire Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (25 reviews)
"Great place clean and quiet "
United States
James P.
The price is HK$876
HK$1,532 total
includes taxes & fees
3 Nov - 4 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

2. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is HK$1,036
HK$2,430 total
includes taxes & fees
2 Nov - 3 Nov
All New Studio apartment in center of town
Building

3. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (13 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is HK$1,035
HK$2,430 total
includes taxes & fees
11 Nov - 12 Nov
All New 1BR with tons of Charm
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

4. New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
The price is HK$1,083
HK$2,492 total
includes taxes & fees
28 Nov - 29 Nov
New Railside Residents
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

5. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is HK$1,976
HK$4,069 total
includes taxes & fees
22 Nov - 23 Nov
#27- Luxury Collection
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

6. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$840
HK$4,095 total
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$1,035
HK$2,430 total
includes taxes & fees
3 Nov - 4 Nov
Once the old Schools house now a newly furnished Apartment
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

8. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"This property was very clean and comfortable; a nicely remodeled apartment in an older home. We had family members staying in one of the other apartments, so it was great to have them so close, but still had privacy. The location is conveniently located with plenty of restaurants nearby, and a short drive to fowntown dining and shops. Karl was an excellent host, griendly and very responsive. Would definitely stay here again!"
United States
Ryan
The price is HK$1,036
HK$2,430 total
includes taxes & fees
25 Nov - 26 Nov
Fully Furnished 1BR Apartment
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, (9 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 HK$1,036
HK$2,430 total
includes taxes & fees
2 Nov - 3 Nov
All New Fully Furnished Cozy Studio
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

10. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is HK$863
HK$1,149 total
includes taxes & fees
2 Nov - 3 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a porch, a front door with a wreath, and a small garden area.

11. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (12 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is HK$883
HK$2,635 total
includes taxes & fees
1 Nov - 2 Nov
Bear Retreat - 2-bedroom house in Waterbury
Stairwell

12. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is HK$727
HK$1,935 total
includes taxes & fees
30 Oct - 31 Oct
Private Apartment in Berlin
A modern living room with a brown leather sofa, a dining area with wooden chairs, a chandelier, and a kitchen with stainless steel appliances.

13. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Plainville
8.8 out of 10, Excellent, (15 reviews)
"Great place and good location."
United States
MARC S.
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

14. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$2,142
HK$4,229 total
includes taxes & fees
30 Oct - 31 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

15. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is HK$720
HK$1,908 total
includes taxes & fees
30 Oct - 31 Oct
2BR Apartment Near Wesleyan 102
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

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

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
The price is HK$624
HK$1,469 total
includes taxes & fees
23 Nov - 24 Nov
One bedroom in United States of America, New Haven
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

17. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
The price is HK$763
HK$1,911 total
includes taxes & fees
2 Nov - 3 Nov
Modern Westville Home near Yale and Hospitals
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

18. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (28 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is HK$541
HK$1,967 total
includes taxes & fees
29 Nov - 30 Nov
The Sun Filled Cozy Creamery
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

19. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is HK$1,004
HK$1,990 total
includes taxes & fees
3 Nov - 4 Nov
Family Stays: Middletown, CT
A house with a front porch, a garage, and a well-maintained lawn.

20. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is HK$1,177
HK$2,755 total
includes taxes & fees
30 Oct - 31 Oct
Angelica’s safe haven @ west haven
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Nice folks. Good location"
john 4-night trip
Posted 3 hours ago
Wyndham Southbury

Find out more about Cheshire

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

  • View our selection of featured holiday rentals in Cheshire
  • Use the map to find apartments and other holiday homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

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?

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 Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, whereas Drazen Orchards and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Roaring Brook 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.