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Cheshire Historic District Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Cheshire Historic District vacation 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 ￥19,124
￥32,854 total
includes taxes & fees
Sep 2 - Sep 3
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
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.
#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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 9 - Aug 10
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.
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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 9 - Aug 10
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 ￥18,573
￥46,386 total
includes taxes & fees
Aug 8 - Aug 9
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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 11 - Aug 12
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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 12 - Aug 13
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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 11 - Aug 12
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 ￥38,568
￥80,397 total
includes taxes & fees
Aug 9 - Aug 10
#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 ￥18,573
￥44,969 total
includes taxes & fees
Aug 27 - Aug 28
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 ￥27,284
￥58,921 total
includes taxes & fees
Aug 4 - Aug 5
#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 ￥63,830
￥117,004 total
includes taxes & fees
Aug 26 - Aug 27
#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 ￥18,573
￥45,913 total
includes taxes & fees
Aug 13 - Aug 14
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 ￥17,314
￥23,059 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥26,837
￥42,078 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥14,449
￥38,652 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥25,094
￥54,671 total
includes taxes & fees
Aug 5 - Aug 6
#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

8/10 Good
"The staff were super friendly. The parking garage was a bit of a pain, but the staff helped us navigate it. The hotel is a little older, but still clean and comfortable. It was a great location just be careful of the bus stop on the corner at night, it seemed a little sketchy."
Tina 1-night trip
Posted 1 hour ago
Omni New Haven Hotel at Yale

Find out more about Cheshire Historic District

Search for holiday rentals in Cheshire Historic District on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire Historic District using one of the methods below:

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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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This vacation 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 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.