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Cheshire Historic District Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 450
AED 763 total
includes taxes & fees
6 Oct - 7 Oct
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
9.4 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 AED 1,006
AED 2,031 total
includes taxes & fees
6 Oct - 7 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, (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 AED 433
AED 1,082 total
includes taxes & fees
4 Oct - 5 Oct
All New Studio apartment in center of town
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,082 total
includes taxes & fees
5 Oct - 6 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.

5. 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 AED 433
AED 1,082 total
includes taxes & fees
4 Oct - 5 Oct
All New Fully Furnished Cozy Studio
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.

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 AED 433
AED 1,071 total
includes taxes & fees
27 Oct - 28 Oct
Newly Remodeled with deck. Close to town center
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is AED 992
AED 2,352 total
includes taxes & fees
3 Oct - 4 Oct
The Cottage by the Woods -private getaway to relax
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

8. 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 AED 916
AED 2,669 total
includes taxes & fees
28 Oct - 29 Oct
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

9. 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 AED 433
AED 1,082 total
includes taxes & fees
4 Oct - 5 Oct
Once the old Schools house now a newly furnished Apartment
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

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 AED 433
AED 1,071 total
includes taxes & fees
11 Oct - 12 Oct
All New Private and Cozy in great location
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

11. #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 AED 582
AED 1,312 total
includes taxes & fees
7 Oct - 8 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.

12. #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 AED 764
AED 1,701 total
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
Building

13. 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 AED 433
AED 1,071 total
includes taxes & fees
12 Oct - 13 Oct
All New 1BR with tons of Charm
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 AED 551
AED 1,456 total
includes taxes & fees
3 Oct - 4 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

15. 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 AED 433
AED 1,082 total
includes taxes & fees
4 Oct - 5 Oct
Brand New Platform #1
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

16. 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 AED 404
AED 538 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a front porch, a garage, and a well-maintained lawn.

17. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is AED 1,719
AED 3,054 total
includes taxes & fees
5 Oct - 6 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A two-story house with a porch, a front door with a wreath, and a small garden area.

18. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 430
AED 1,207 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
Stairwell

19. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AED 437
AED 1,028 total
includes taxes & fees
6 Oct - 7 Oct
Private Apartment in Berlin
A spacious living room with large windows, a fireplace, and a view of the outdoors.

20. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is AED 1,003
AED 1,980 total
includes taxes & fees
4 Oct - 5 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Nice clean hotel and wonderful staff."
Michael 1-night trip
Posted 10 hours ago
Best Western Executive Hotel Of New Haven - West Haven

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.