Cheshire Historic District Holiday Rentals from €189: Search Short-Term Rentals

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Our top choices for Cheshire Historic District holiday rentals

A wooden porch with a concrete step leading to a door.

1. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire

James P.

includes taxes & fees

14 Dec - 15 Dec

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

2. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

"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."

Cindy M.

includes taxes & fees

29 Nov - 30 Nov

A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

3. Brand New Platform #1

Wallingford Center

Cherie G.

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

Wallingford

Alan

includes taxes & fees

9 Dec - 10 Dec

A kitchen with dark cabinets, a black refrigerator, a microwave, and a granite countertop island.

5. Fully Furnished 1BR Apartment

Wallingford

"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!"

Ryan

includes taxes & fees

25 Nov - 26 Nov

A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

6. All New Studio apartment in center of town

Wallingford Center

DAVID B.

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.

7. Newly Remodeled with deck. Close to town center

Wallingford

Karen F.

includes taxes & fees

14 Dec - 15 Dec

A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

8. New Railside Residents

Wallingford Center

Thomas S.

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

Wallingford Center

Jeanette W.

includes taxes & fees

23 Nov - 24 Nov

A kitchen with a dining table, chairs, and a brick wall.

10. All New Private and Cozy in great location

Wallingford

ROBERT P.

A white door with a glass panel, a white picket fence, and a wooden porch.

11. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Igor L.

includes taxes & fees

22 Nov - 23 Nov

12. All New 1BR with tons of Charm

Wallingford Center

Hannah Z.

includes taxes & fees

14 Dec - 15 Dec

A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

13. All New Fully Furnished Cozy Studio

Wallingford Center

Rick C.

A modern kitchen with white cabinets, a stainless steel stove, and a black faucet.

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

Dwight

Stephanie G.

includes taxes & fees

7 Dec - 8 Dec

A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

15. Private Apartment in Southbury 102

Southbury

Debbie P.

includes taxes & fees

28 Nov - 29 Nov

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

Wolcott

David G.

includes taxes & fees

30 Nov - 1 Dec

17. Private Apartment in Berlin

Berlin

Shaun L.

includes taxes & fees

16 Nov - 17 Nov

A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

18. The Sun Filled Cozy Creamery

Plainville

Heather T.

includes taxes & fees

29 Nov - 30 Nov

A living room with a brick fireplace, white furniture, and a patterned rug.

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

Meriden

includes taxes & fees

14 Dec - 15 Dec

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

20. Stylish Westville Apartment near Yale Campus

West New Haven

Northeast C.

includes taxes & fees

16 Nov - 17 Nov

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Top Cheshire Historic District Hotel Reviews

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Comfortable room, quiet, and good location"

Clarion Inn North Haven - New Haven North

8/10 Good

"The hotel is undergoing renovations so it's not as clean as it could be. The updated rooms are really nice but it needed a few things. 1) Rooms needs a hairdryer 2) also needs a 2nd trash can 3) Coffeemaker doesnt work right The breakfast was ok but it wasnt bad either. The bathrooms was tootier. Love the double shower heads and the toiletries. Helped with not having to pack my own. Overall I would stay here again. Hopefully it's cleaner after renovations are done. And the chemical rug smell goes away."

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, apart-hotels, 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 favorite 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 depends 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 €189 per night. Entering your travel dates in the search wizard 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 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?

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy: This holiday home rental outside of Cheshire Historic District is located on the waterfront, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.

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Check prices for these dates

Our top choices for Cheshire Historic District holiday rentals

1. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.