Cheshire Holiday Rentals from AU$419: Search Short-Term Rentals

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Our top choices for Cheshire holiday 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.

Cheshire

James P.

includes taxes & fees

2 Nov - 3 Nov

A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

2. 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

21 Oct - 22 Oct

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

Wallingford Center

Jeanette W.

includes taxes & fees

21 Oct - 22 Oct

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

Wallingford Center

DAVID B.

includes taxes & fees

27 Oct - 28 Oct

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

Wallingford Center

Rick C.

includes taxes & fees

21 Oct - 22 Oct

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

Wallingford

Karen F.

includes taxes & fees

18 Nov - 19 Nov

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

7. New Railside Residents

Wallingford Center

Thomas S.

includes taxes & fees

16 Nov - 17 Nov

A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

8. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Waterbury

Dirk N.

includes taxes & fees

26 Oct - 27 Oct

9. All New 1BR with tons of Charm

Wallingford Center

Hannah Z.

includes taxes & fees

10 Nov - 11 Nov

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

10. 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

28 Oct - 29 Oct

A two-story house with a porch, a front door with a wreath, and a small garden area.

11. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Radha

includes taxes & fees

21 Oct - 22 Oct

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

12. The Sun Filled Cozy Creamery

Plainville

Heather T.

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

13. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Watertown

Laurie P.

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

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

Dwight

Stephanie G.

includes taxes & fees

2 Nov - 3 Nov

A white house with a wooden staircase leading to a porch.

15. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Niki B.

includes taxes & fees

1 Nov - 2 Nov

A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

16. 2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

includes taxes & fees

21 Oct - 22 Oct

A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

17. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

Plainville

MARC S.

includes taxes & fees

22 Oct - 23 Oct

18. Private Apartment in Berlin

Berlin

Shaun L.

includes taxes & fees

3 Nov - 4 Nov

A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

19. Prime Yale Studio Steps to Sallys Apizza

Downtown New Haven

Milton W.

includes taxes & fees

21 Oct - 22 Oct

A hotel room with a bed, bedside lamps, a table, a chair, an air conditioning unit, and a window with curtains.

20. 1 Queen Bed | Wethersfield

Wethersfield

Anonymous traveller

includes taxes & fees

6 Nov - 7 Nov

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Top Cheshire Hotel Reviews

Cambria Hotel New Haven University Area

8/10 Good

"Nice stay, convenient spot"

Best Western Hartford Hotel & Suites

8/10 Good

"This is an older motel.... room was clean and well stocked. Our room was at the end of a hallway and a convenient entry door at the back of the building. Parking was plentiful and with handicapped tag, as we were right next to the door. I am glad on my reservation I made a comment that we preferred a ground level room if there is no elevator. Inside this back entry door was a set of stairs going to the second level.... very hard to lug suitcases etc. up steps for seniors. Breakfast area is pleasant and a variety of hot sausage and eggs and bagels, muffins, etc Something I had never seen before was premade French toast....heat up in the toaster and enjoy with butter/syrup. A variety of juices and coffee available. My husband went down there one morning and found none of the containers were being refilled and it wasn't that late. This stayed open until 10 am which is later than most other motel/hotel breakfast areas."

Find out more about Cheshire

Everything you need to know about Cheshire 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 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Cheshire holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire 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 holiday rentals we have selected for you start as low as AU$419 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire 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 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 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. 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 a holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Cheshire Hollow Farm, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best holiday rentals that Cheshire has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Cheshire is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Cheshire?

Family-friendly attractions include Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, whereas Drazen Orchards and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Roaring Brook Park are other places worth a visit.

What’s a holiday rental in Cheshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheshire. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.

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Check prices for these dates

Our top choices for Cheshire holiday rentals

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

2. Fully Furnished 1BR Apartment

3. Once the old Schools house now a newly furnished Apartment

4. All New Studio apartment in center of town

5. All New Fully Furnished Cozy Studio

6. Newly Remodeled with deck. Close to town center

7. New Railside Residents

8. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

9. All New 1BR with tons of Charm

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

11. Bear Retreat - 2-bedroom house in Waterbury

12. The Sun Filled Cozy Creamery

13. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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

15. Cozy One Bedroom Apartment Centrally Located in Southbury

16. 2BR Apartment Near Wesleyan 102

17. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

18. Private Apartment in Berlin

19. Prime Yale Studio Steps to Sallys Apizza

20. 1 Queen Bed | Wethersfield

Find holiday rentals that suit your style

Top Cheshire Hotel Reviews

Cambria Hotel New Haven University Area

Hyatt Place Milford / New Haven

Best Western Hartford Hotel & Suites

Cheshire Welcome Inn

Omni New Haven Hotel at Yale

Red Roof Inn Meriden

Clarion Inn North Haven - New Haven North

The Capitol Hotel

Find out more about Cheshire

Frequently asked questions

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