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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Cheshire Historic District 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, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is £161
includes taxes & fees
3 Nov - 4 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A spacious living area with a sofa, a dining table, and a kitchen in the background.

2. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.6 out of 10, Exceptional, (4 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is £374
includes taxes & fees
12 Oct - 13 Oct
#43- Modern Luxury Log Cabin Retreat - Fire Pit
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

3. 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 £227
includes taxes & fees
16 Oct - 17 Oct
All New Studio apartment in center of town
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

4. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is £227
includes taxes & fees
11 Oct - 12 Oct
Once the old Schools house now a newly furnished Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

5. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is £227
includes taxes & fees
11 Oct - 12 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

6. 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 £227
includes taxes & fees
8 Oct - 9 Oct
All New Fully Furnished Cozy Studio
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

7. 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.
The price is £227
includes taxes & fees
11 Oct - 12 Oct
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.

8. 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 £223
includes taxes & fees
7 Nov - 8 Nov
Newly Remodeled with deck. Close to town center
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 £227
includes taxes & fees
11 Oct - 12 Oct
All New Private and Cozy in great location
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

10. 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 £545
includes taxes & fees
1 Nov - 2 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is £482
includes taxes & fees
8 Oct - 9 Oct
The Cottage by the Woods -private getaway to relax
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

12. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is £270
includes taxes & fees
11 Oct - 12 Oct
#23 COMFORT & LUXURY 3 BR/2 BA House
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

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 £345
includes taxes & fees
21 Oct - 22 Oct
#27- Luxury Collection
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

14. 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 £308
includes taxes & fees
11 Oct - 12 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
Building

15. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is £227
includes taxes & fees
12 Oct - 13 Oct
All New 1BR with tons of Charm
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

16. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
#30 - Spacious & Cozy!
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

17. 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 £227
includes taxes & fees
21 Oct - 22 Oct
Brand New Platform #1
A living room with a sectional sofa, a wooden coffee table, a lamp, and a ceiling fan.

18. #25 Massive 5 BR in Downtown Southington

#25 Massive 5 BR in Downtown Southington
Southington
9.0 out of 10, Wonderful, (4 reviews)
"The house was perfect. We came in for my son’s wedding and had family staying from all over- Canada, Arkansas and Florida. The house worked out perfect. All the rooms are large and the beds are very comfortable. Kitchen is well stocked. There is a bit of a steep staircase to enter the house which can be tricky for the elderly but completely doable. I would definitely rent this property again if needed."
United States
michelle d.
The price is £350
includes taxes & fees
14 Oct - 15 Oct
#25 Massive 5 BR in Downtown Southington
Living area

19. Old Silver factory converted to a new 1Br with all the charm

Old Silver factory converted to a new 1Br with all the charm
Wallingford Center
The price is £227
includes taxes & fees
12 Oct - 13 Oct
Old Silver factory converted to a new 1Br with all the charm
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

20. 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 £113
includes taxes & fees
12 Oct - 13 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
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

New Haven Hotel

New Haven Hotel

8/10 Good
"Room is average but more spacious than we thought. AC fan is loud. TV remote is sticky, it might not be wiped and cleaned for a while. Location is good but parking is a problem. Public parking lot charges less if you check out early. Reception people are indifferent and reluctant to introduce details about the hotel."
Zhihao 1-night trip
Posted 8 hours ago
New Haven Hotel

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cheshire Historic District holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire Historic District holiday rentals we have selected for you start as low as £120 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 holiday 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 holiday.

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 holiday rentals in Cheshire Historic District?

Yes, there are holiday rentals close to the most popular sights in Cheshire Historic District, or you can select a more 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 holiday rentals that Cheshire Historic District has to offer?

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy: This holiday home rental outside of Cheshire Historic District is located on the waterfront, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are holiday rentals like in Cheshire Historic District?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire Historic District. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.