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

Cheshire Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Cheshire vacation 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, (26 reviews)
"Great place clean and quiet "
United States
James P.
The price is CA $170
CA $277 total
includes taxes & fees
Dec 7 - Dec 8
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

2. 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 CA $113
CA $661 total
includes taxes & fees
Nov 20 - Nov 21
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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.

3. 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 CA $186
CA $412 total
includes taxes & fees
Nov 23 - Nov 24
Newly Remodeled with deck. Close to town center
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 CA $186
CA $412 total
includes taxes & fees
Dec 1 - Dec 2
Fully Furnished 1BR Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

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, (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 CA $186
CA $412 total
includes taxes & fees
Nov 23 - Nov 24
All New Studio apartment in center of town
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is CA $186
CA $412 total
includes taxes & fees
Nov 23 - Nov 24
Once the old Schools house now a newly furnished Apartment
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

7. 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 CA $186
CA $412 total
includes taxes & fees
Nov 16 - Nov 17
New Railside Residents
Building

8. 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 CA $186
CA $422 total
includes taxes & fees
Nov 23 - Nov 24
All New 1BR with tons of Charm
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

9. 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 CA $155
CA $196 total
includes taxes & fees
Nov 13 - Nov 14
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

10. #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 CA $356
CA $703 total
includes taxes & fees
Nov 23 - Nov 24
#27- Luxury Collection
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

11. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
The price is CA $186
CA $422 total
includes taxes & fees
Nov 11 - Nov 12
Brand New Platform #1
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

12. 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 CA $186
CA $412 total
includes taxes & fees
Nov 16 - Nov 17
All New Fully Furnished Cozy Studio
A two-story house with a porch, a front door with a wreath, and a small garden area.

13. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Very clean, all you need away from home, super !!!"
United States
Igor L.
The price is CA $164
CA $465 total
includes taxes & fees
Nov 23 - Nov 24
Bear Retreat - 2-bedroom house in Waterbury
Stairwell

14. 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 CA $156
CA $366 total
includes taxes & fees
Nov 11 - Nov 12
Private Apartment in Berlin
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 CA $97
CA $330 total
includes taxes & fees
Nov 29 - Nov 30
The Sun Filled Cozy Creamery
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 CA $108
CA $241 total
includes taxes & fees
Nov 30 - Dec 1
One bedroom in United States of America, New Haven
Interior

17. 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.
The price is CA $163
CA $311 total
includes taxes & fees
Nov 15 - Nov 16
Château Blanc | Near Yale University
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

18. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
The price is CA $166
CA $357 total
includes taxes & fees
Nov 17 - Nov 18
Prime Yale Studio Steps to Sallys Apizza
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

19. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is CA $141
CA $343 total
includes taxes & fees
Nov 11 - Nov 12
2BR Apartment Near Wesleyan 102
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.
The price is CA $146
CA $334 total
includes taxes & fees
Dec 9 - Dec 10
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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

8/10 Good
"I had a very nice stay. I was there for a 2 nights stay. The room was clean. The staff very nice and helpful. Breakfast was bad. The hard boiled eggs were icy cold. The frozen waffles were really disgusting. There was really nothing good or delicious about breakfast. I ended up going to a restaurant for breakfast. Overall everything else was good except the breakfast."
Marjorie 1-night trip
Posted 2 hours ago
Hyatt Place Milford / New Haven

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire vacation rentals we have selected for you start as low as CA $431 per night. Entering your travel dates in the search wizard 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. 

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Cheshire Hollow Farm, 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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Cheshire vacation home rental. It is located on the beach and has a balcony, a barbecue grill, 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 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 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.