Cheshire Historic District 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 Historic District 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 $169
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 21 - Nov 22
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

3. 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 $422 total
includes taxes & fees
Nov 26 - Nov 27
Fully Furnished 1BR Apartment
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

4. 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 $195
CA $433 total
includes taxes & fees
Nov 14 - Nov 15
Brand New Platform #1
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 CA $186
CA $422 total
includes taxes & fees
Nov 16 - Nov 17
Newly Remodeled with deck. Close to town center
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

6. 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 19 - Nov 20
All New Studio apartment in center of town
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 CA $186
CA $404 total
includes taxes & fees
Nov 12 - Nov 13
Once the old Schools house now a newly furnished Apartment
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 CA $186
CA $422 total
includes taxes & fees
Nov 16 - Nov 17
New Railside Residents
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

9. 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.
The price is CA $186
CA $422 total
includes taxes & fees
Nov 26 - Nov 27
All New Private and Cozy in great location
Building

10. 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 $404 total
includes taxes & fees
Nov 12 - Nov 13
All New 1BR with tons of Charm
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

11. 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 $422 total
includes taxes & fees
Nov 16 - Nov 17
All New Fully Furnished Cozy Studio
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

12. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is CA $212
CA $541 total
includes taxes & fees
Nov 30 - Dec 1
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

13. #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 $357
CA $710 total
includes taxes & fees
Nov 23 - Nov 24
#27- Luxury Collection
A room with a fireplace, two sofas, a rug, and a robotic vacuum cleaner.

14. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is CA $424
CA $916 total
includes taxes & fees
Nov 12 - Nov 13
The Cottage by the Woods -private getaway to relax
A hallway with a white door, a floral wall decoration, a vacuum cleaner, and a wall-mounted candle holder.

15. 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 $165
CA $467 total
includes taxes & fees
Nov 22 - Nov 23
Bear Retreat - 2-bedroom house in Waterbury
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 $246 total
includes taxes & fees
Nov 30 - Dec 1
One bedroom in United States of America, New Haven
Stairwell

17. 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 $141
CA $344 total
includes taxes & fees
Nov 12 - Nov 13
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.

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 CA $98
CA $340 total
includes taxes & fees
Nov 29 - Nov 30
The Sun Filled Cozy Creamery
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

19. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
9.2 out of 10, Wonderful, (5 reviews)
"Convenient location & hosts"
United States
Northeast C.
The price is CA $147
CA $348 total
includes taxes & fees
Nov 24 - Nov 25
Stylish Westville Apartment near Yale Campus
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 Historic District Hotel Reviews

An outdoor patio area with a stone fire pit, wicker furniture, and a bar area with a flat-screen TV.
Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden
Hamden

10/10 Excellent

Clean room
Canada
Jintong
Reviewed October 30, 2026
Residence Inn by Marriott New Haven Hamden

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District 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 Historic District 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 Historic District vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire Historic District vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire Historic District. 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 Historic District 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 Historic District vacation rentals we have selected for you start as low as CA $113 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire Historic District rentals

At Expedia, we put the best Cheshire Historic District 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 Historic District 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 Historic District 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 Historic District. 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 vacation rentals in Cheshire Historic District?

Yes, there are vacation rentals near popular sights in Cheshire Historic District, or you can go with a secluded option if you're looking for a relaxing stay. Cheshire Historic District is known for its churches and university setting.

What are some of the best vacation home rentals in Cheshire Historic District?

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy: This vacation home rental outside of Cheshire Historic District is located on the waterfront and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Cheshire Historic District?

Explore the area and family-friendly sights such as Lake Compounce, or get out into nature at a spot like Mount Carmel. In the larger area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are vacation rentals like in Cheshire Historic District?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Cheshire Historic District. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.