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
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$1,035
HK$2,430 total
includes taxes & fees
2 Nov - 3 Nov
All New Studio apartment in center of town
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

3. 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
2 Nov - 3 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.

4. 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$1,035
HK$2,430 total
includes taxes & fees
25 Nov - 26 Nov
Fully Furnished 1BR Apartment
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 HK$1,035
HK$2,430 total
includes taxes & fees
2 Nov - 3 Nov
Newly Remodeled with deck. Close to town center
Building

6. 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
2 Nov - 3 Nov
All New 1BR with tons of Charm
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

7. 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 modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

8. 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$1,035
HK$2,430 total
includes taxes & fees
16 Nov - 17 Nov
New Railside Residents
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

9. 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 compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

10. 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$1,083
HK$2,492 total
includes taxes & fees
29 Nov - 30 Nov
All New Fully Furnished Cozy Studio
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
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

12. #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
Stairwell

13. 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 kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

14. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
2BR Apartment Near Wesleyan 301
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

15. 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 modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

16. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (7 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$678
HK$1,719 total
includes taxes & fees
30 Oct - 31 Oct
Private Apartment in Southbury 102
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

17. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveller
The price is HK$532
HK$612 total
includes taxes & fees
6 Nov - 7 Nov
1 Queen Bed | Wethersfield
A hotel room with a bed, bedside table with a phone, a desk with a chair, a TV, and a door leading to another room.

18. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Before morning travel, we got much-needed rest here. Rooms had ample space so it didn't feel cramped at all, plus friendly staff shared helpful breakfast recommendations as part of our group treat experience."
United States
Anonymous traveller
The price is HK$631
HK$725 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1 King Bed | Smoking
A row of brownstone buildings with a central staircase leading to the second floor.

19. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (17 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is HK$847
HK$1,910 total
includes taxes & fees
1 Nov - 2 Nov
Bright Downtown Studio near Yale & East Rock!
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

20. 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.
Modern Westville Home near Yale and Hospitals
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Excellent Customer service over the phone and in person!"
Calnetha 1-night trip
Posted 6 hours ago
Best Western Executive Hotel Of New Haven - West Haven

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.