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

Cheshire Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Cheshire vacation rentals

Smart TV

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, (22 reviews)
"Great place clean and quiet "
United States
James P.
$180 nightly
The price is $204
Sep 1 - Sep 2
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Coffee/tea maker, fridge, microwave, oven

2. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
$278 nightly
The price is $296
Sep 6 - Sep 7
Total with taxes and fees
Fully Furnished 1BR Apartment
Coffee/tea maker, fridge, microwave, oven

3. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (8 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.
$277 nightly
The price is $295
Sep 12 - Sep 13
Total with taxes and fees
All New Fully Furnished Cozy Studio
TV

4. 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.
$278 nightly
The price is $296
Sep 10 - Sep 11
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Exterior

5. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
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.
$278 nightly
The price is $296
Aug 26 - Aug 27
Total with taxes and fees
All New Studio apartment in center of town
1 bedroom, iron/ironing board, WiFi, bed sheets

6. 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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$278 nightly
The price is $296
Aug 30 - Aug 31
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
TV

7. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
$278 nightly
The price is $296
Aug 19 - Aug 20
Total with taxes and fees
All New Private and Cozy in great location
TV

8. Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
8.0 out of 10, Very Good, (1 review)
"There were minor cleaning issues in the bathroom, and my only/biggest complaint is the listing is misleading as it says you have no neighbors but the space is physically attached to a larger house and the driveway and entry/exit doors for both units open into the same small space. Additionally the front door has a large glass window with no curtains so you have absolutely no privacy. This is a direct conflict with the listing and I did bring this up to the landlord. That being said the location...
United States
Zackary G.
$201 nightly
The price is $216
Aug 21 - Aug 22
Total with taxes and fees
Tiny, Budget Friendly 1 Bedroom Central CT
Exterior

9. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$278 nightly
The price is $296
Aug 19 - Aug 20
Total with taxes and fees
All New 1BR with tons of Charm
Interior

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.
$130 nightly
The price is $147
Sep 8 - Sep 9
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Coffee/tea maker, fridge, microwave, oven

11. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
$566 nightly
The price is $614
Sep 7 - Sep 8
Total with taxes and fees
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

12. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$239 nightly
The price is $254
Aug 18 - Aug 19
Total with taxes and fees
The Sun Filled Cozy Creamery
Interior

13. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
$163 nightly
The price is $184
Aug 19 - Aug 20
Total with taxes and fees
Château Blanc | Near Yale University
Coffee/tea maker, fridge, microwave, oven

14. #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.
$712 nightly
The price is $780
Aug 29 - Aug 30
Total with taxes and fees
#27- Luxury Collection
1 bedroom, desk, iron/ironing board, WiFi

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

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
$159 nightly
The price is $180
Aug 18 - Aug 19
Total with taxes and fees
One bedroom in United States of America, New Haven
Dining

16. 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, (79 reviews)
"Spacious"
United States
Mehul
$206 nightly
The price is $233
Sep 5 - Sep 6
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

17. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (15 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
$216 nightly
The price is $245
Aug 18 - Aug 19
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
Interior

18. 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.
$215 nightly
The price is $244
Aug 18 - Aug 19
Total with taxes and fees
Modern Westville Home near Yale and Hospitals
TV, fireplace

19. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
$594 nightly
The price is $642
Aug 26 - Aug 27
Total with taxes and fees
#41- Available 12/8! - sleeps 14
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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

8/10 Good
"Peace and Quiet. Great night sleep. Enjoy my weekend getaway. Will return."
Greg 1-night trip
Posted 2 hours ago
Hilton Garden Inn Milford

Find out more about Cheshire

Everything you need to know about Cheshire vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cheshire in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Drazen Orchards, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers 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 vacation home rentals in Cheshire?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: Visitors like this Cheshire vacation home rental. It is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, 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 vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.