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Cheshire Historic District Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Cheshire Historic District holiday 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, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AU$292
includes taxes & fees
29 Sept - 30 Sept
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Exterior

2. 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 AU$410
includes taxes & fees
3 Oct - 4 Oct
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, WiFi, bed sheets

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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$410
includes taxes & fees
4 Oct - 5 Oct
Once the old Schools house now a newly furnished Apartment
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.
The price is AU$412
includes taxes & fees
23 Sept - 24 Sept
Newly Remodeled with deck. Close to town center
TV

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 AU$413
includes taxes & fees
20 Sept - 21 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

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, (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.
The price is AU$411
includes taxes & fees
29 Sept - 30 Sept
All New Studio apartment in center of town
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.
The price is AU$399
includes taxes & fees
19 Oct - 20 Oct
All New Private and Cozy in great location
TV

8. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 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 AU$641
includes taxes & fees
23 Sept - 24 Sept
#43- Modern Luxury Log Cabin Retreat - Fire Pit
Coffee/tea maker, fridge, microwave, oven

9. 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 AU$413
includes taxes & fees
21 Sept - 22 Sept
All New Fully Furnished Cozy Studio
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.
The price is AU$209
includes taxes & fees
30 Sept - 1 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
TV

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 AU$399
includes taxes & fees
19 Oct - 20 Oct
Brand New Platform #1
Iron/ironing board, WiFi, bed sheets

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is AU$890
includes taxes & fees
23 Sept - 24 Sept
The Cottage by the Woods -private getaway to relax
TV

13. 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 AU$410
includes taxes & fees
5 Oct - 6 Oct
Old Silver factory converted to a new 1Br with all the charm
TV

14. 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.
The price is AU$302
includes taxes & fees
28 Sept - 29 Sept
Tiny, Budget Friendly 1 Bedroom Central CT
Exterior detail

15. 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 AU$548
includes taxes & fees
2 Oct - 3 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
Interior

16. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AU$175
includes taxes & fees
23 Sept - 24 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior detail

17. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (7 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AU$479
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
Smart TV

18. #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 AU$548
includes taxes & fees
11 Oct - 12 Oct
#23 COMFORT & LUXURY 3 BR/2 BA House
Coffee/tea maker, fridge, microwave, oven

19. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AU$380
includes taxes & fees
22 Sept - 23 Sept
Private Apartment in Southbury 103
Coffee/tea maker, fridge, microwave, oven

20. #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 AU$645
includes taxes & fees
5 Oct - 6 Oct
#27- Luxury Collection
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"Pool being closed"
Christopher 1-night trip
Posted 8 hours ago
Holiday Inn Express Southington by IHG

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, 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 favourite 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 depend 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 AU$328 per night. Entering your travel dates in the search wizard might find you 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.