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Cheshire Historic District Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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
9.2 out of 10, Wonderful, (21 reviews)
"Great place clean and quiet "
United States
James P.
The price is AU$316
includes taxes & fees
1 Sept - 2 Sept
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
House (3 Bedrooms) | Interior

2. Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
The price is AU$672
includes taxes & fees
3 Aug - 4 Aug
Lakefront Home, Close to Mt Southington!
TV

3. #43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 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$651
includes taxes & fees
3 Aug - 4 Aug
#43- Modern Luxury Log Cabin Retreat | Fire Pit
TV

4. 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)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is AU$417
includes taxes & fees
9 Aug - 10 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
Property grounds

5. Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
Wolcott
10.0 out of 10, Exceptional, (33 reviews)
"This was such a beautiful house, my family enjoyed it all, the view, the lake and the kayaking. House was clean, host was amazing, made our stay one for the books, will definitely book again."
United States
Yogesh R.
The price is AU$618
includes taxes & fees
3 Aug - 4 Aug
Lakefront Home, Close to Mt Southington!
TV

6. 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$417
includes taxes & fees
3 Aug - 4 Aug
Newly Remodeled with deck. Close to town center
1 bedroom, iron/ironing board, WiFi, bed sheets

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, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$417
includes taxes & fees
3 Aug - 4 Aug
Once the old Schools house now a newly furnished Apartment
Exterior

8. 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$417
includes taxes & fees
8 Aug - 9 Aug
All New Studio apartment in center of town
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.
The price is AU$415
includes taxes & fees
11 Aug - 12 Aug
All New 1BR with tons of Charm
TV

10. 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$415
includes taxes & fees
13 Aug - 14 Aug
All New Private and Cozy in great location
Interior

11. 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 AU$415
includes taxes & fees
11 Aug - 12 Aug
New Railside Residents
Coffee/tea maker, fridge, microwave, oven

12. #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.
The price is AU$732
includes taxes & fees
9 Aug - 10 Aug
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
TV

13. All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is AU$422
includes taxes & fees
24 Aug - 25 Aug
All new 1BR apartment with all the features you are looking for
Smart TV

14. #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$525
includes taxes & fees
4 Aug - 5 Aug
#23 *COMFORT & LUXURY* 3 BR/2 BA House
TV, fireplace

15. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AU$1,040
includes taxes & fees
26 Aug - 27 Aug
#41- Available 12/8! - sleeps 14
TV

16. 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$415
includes taxes & fees
13 Aug - 14 Aug
Old Silver factory converted to a new 1Br with all the charm
Interior

17. 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$212
includes taxes & fees
1 Sept - 2 Sept
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

18. Modern Studio Retreat

Modern Studio Retreat
Dwight
10.0 out of 10, Exceptional, (1 review)
The price is AU$387
includes taxes & fees
1 Sept - 2 Sept
Modern Studio Retreat
Interior

19. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is AU$406
includes taxes & fees
5 Aug - 6 Aug
Private Apartment in Berlin
Property grounds

20. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is AU$493
includes taxes & fees
6 Aug - 7 Aug
#24 *Serenity* A Lakefront Cottage Retreat
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"We stayed overnight for our anniversary and had a pleasant stay. The staff were welcoming, the bed was very comfortable, and the bathroom clean. We will definitely be back."
Bethany 1-night trip
Posted 2 hours ago
Omni New Haven Hotel at Yale

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$202 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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This holiday home rental outside of Cheshire Historic District is equipped with a patio, air conditioning and a Smart TV to help you feel comfortable during your stay.

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.