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Cheshire Historic District Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 CA $171
CA $289 total
includes taxes & fees
Sep 29 - Sep 30
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

2. 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)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is CA $167
CA $415 total
includes taxes & fees
Sep 27 - Sep 28
Once the old Schools house now a newly furnished Apartment
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

3. 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 CA $167
CA $415 total
includes taxes & fees
Sep 27 - Sep 28
All New Fully Furnished Cozy Studio
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

4. 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 CA $167
CA $410 total
includes taxes & fees
Sep 29 - Sep 30
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.

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 CA $167
CA $413 total
includes taxes & fees
Oct 5 - Oct 6
Newly Remodeled 1-BR Close to Everything yet Very Private
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

6. 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 CA $167
CA $410 total
includes taxes & fees
Sep 30 - Oct 1
All New Private and Cozy in great location
A spacious living area with a sofa, a dining table, and a kitchen in the background.

7. #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 CA $387
CA $789 total
includes taxes & fees
Oct 6 - Oct 7
#43- Modern Luxury Log Cabin Retreat - Fire Pit
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

8. 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 CA $167
CA $415 total
includes taxes & fees
Sep 27 - Sep 28
Brand New Platform #1
A compact kitchen with wooden cabinets, a microwave, a sink, and a chair.

9. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
The price is CA $106
CA $150 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Studio apartment in delightful Waterbury with Central Air
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

10. #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 CA $244
CA $530 total
includes taxes & fees
Oct 7 - Oct 8
#23 COMFORT & LUXURY 3 BR/2 BA House

11. 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 CA $167
CA $411 total
includes taxes & fees
Oct 12 - Oct 13
All New 1BR with tons of Charm
A kitchen with a ceiling fan, a dining area with a table and chairs, and a living room with a sofa and a plant.

12. 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 CA $124
CA $286 total
includes taxes & fees
Sep 28 - Sep 29
Tiny, Budget Friendly 1 Bedroom Central CT
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is CA $382
CA $901 total
includes taxes & fees
Sep 27 - Sep 28
The Cottage by the Woods -private getaway to relax

14. 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 CA $167
CA $415 total
includes taxes & fees
Sep 27 - Sep 28
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.

15. 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 CA $156
CA $207 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

16. 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 CA $212
CA $565 total
includes taxes & fees
Oct 1 - Oct 2
1-bedroom vacation home 22 minutes from Quinnipiac University
A two-story house with a porch, a front door with a wreath, and a small garden area.

17. 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 CA $165
CA $463 total
includes taxes & fees
Oct 8 - Oct 9
Bear Retreat - 2-bedroom house in Waterbury
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

18. #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.
The price is CA $310
CA $721 total
includes taxes & fees
Oct 7 - Oct 8
#30 - Spacious & Cozy!

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 CA $157
CA $381 total
includes taxes & fees
Sep 28 - Sep 29
Private Apartment in Berlin
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

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 CA $310
CA $678 total
includes taxes & fees
Oct 5 - Oct 6
#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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good
"Breakfast was great! Staff were friendly and helpful"
Greg 1-night trip
Posted less than an hour ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Cheshire Historic District

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cheshire Historic District. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Cheshire Hollow Farm, 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.