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Cheshire Historic District Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (25 reviews)
"Great place clean and quiet "
United States
James P.
$172 nightly
The price is $194
Nov 3 - Nov 4
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

2. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"This property was very clean and comfortable; a nicely remodeled apartment in an older home. We had family members staying in one of the other apartments, so it was great to have them so close, but still had privacy. The location is conveniently located with plenty of restaurants nearby, and a short drive to fowntown dining and shops. Karl was an excellent host, griendly and very responsive. Would definitely stay here again!"
United States
Ryan
$299 nightly
The price is $320
Nov 20 - Nov 21
Total with taxes and fees
Fully Furnished 1BR Apartment
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$290 nightly
The price is $310
Oct 26 - Oct 27
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
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, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
$290 nightly
The price is $310
Oct 26 - Oct 27
Total with taxes and fees
All New Studio apartment in center of town
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.
$290 nightly
The price is $310
Oct 26 - Oct 27
Total with taxes and fees
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.
$293 nightly
The price is $313
Oct 27 - Oct 28
Total with taxes and fees
Newly Remodeled with deck. Close to town center
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

7. 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.
$290 nightly
The price is $310
Nov 16 - Nov 17
Total with taxes and fees
New Railside Residents
Building

8. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (13 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
$290 nightly
The price is $310
Oct 26 - Oct 27
Total with taxes and fees
All New 1BR with tons of Charm
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

9. 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.
$130 nightly
The price is $147
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A kitchen with a stainless steel stove, oven, and microwave.

10. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$297 nightly
The price is $336
Nov 1 - Nov 2
Total with taxes and fees
Bear Retreat - 2-bedroom house in Waterbury
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

11. 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.
$511 nightly
The price is $579
Oct 28 - Oct 29
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
$566 nightly
The price is $640
Oct 24 - Oct 25
Total with taxes and fees
The Cottage by the Woods -private getaway to relax
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

13. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
$183 nightly
The price is $208
Oct 25 - Oct 26
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

14. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
9.0 out of 10, Wonderful, (4 reviews)
"Great location, well organized space, well decorated. I loved that there were enough places to sit and be comfortable, many VRBO’s have tiny little sofas that are so uncomfortable, but this has proper furniture. The beds are very firm."
Canada
Alex C.
$218 nightly
The price is $247
Oct 26 - Oct 27
Total with taxes and fees
Stylish Westville Apartment near Yale Campus
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

15. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
$157 nightly
The price is $177
Oct 25 - Oct 26
Total with taxes and fees
One bedroom in United States of America, New Haven
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

16. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (27 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
$238 nightly
The price is $253
Nov 16 - Nov 17
Total with taxes and fees
The Sun Filled Cozy Creamery
A room with a wooden floor, a white door, and a closet with hanging clothes and a folded towel.

17. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Newhallville
$367 nightly
The price is $415
Oct 26 - Oct 27
Total with taxes and fees
Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale
Stairwell

18. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
$230 nightly
The price is $260
Oct 26 - Oct 27
Total with taxes and fees
Private Apartment in Berlin
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

19. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (7 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
$223 nightly
The price is $253
Oct 26 - Oct 27
Total with taxes and fees
Private Apartment in Southbury 102
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

20. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$231 nightly
The price is $261
Oct 26 - Oct 27
Total with taxes and fees
2BR Apartment Near Wesleyan 102
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
"helpful staff and very clean room"
Robert 2-night trip
Posted 13 hours ago
Omni New Haven Hotel at Yale

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire Historic District vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cheshire Historic District in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cheshire Historic District rentals

At Expedia, we put the best Cheshire Historic District vacation 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 vacation.

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 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.