Cheshire Vacation Rentals from AED 253: Search Short-Term Rentals

A stone tower with a metal gate, surrounded by trees and a stone wall.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cheshire 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.

Cheshire

James P.

AED 694 total

includes taxes & fees

14 Dec - 15 Dec

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

2. Brand New Platform #1

Wallingford Center

Cherie G.

AED 1,119 total

includes taxes & fees

14 Nov - 15 Nov

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

3. 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.

AED 1,715 total

includes taxes & fees

20 Nov - 21 Nov

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

AED 1,057 total

includes taxes & fees

9 Dec - 10 Dec

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

5. All New Studio apartment in center of town

Wallingford Center

DAVID B.

AED 1,094 total

includes taxes & fees

19 Nov - 20 Nov

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.

AED 1,094 total

includes taxes & fees

16 Nov - 17 Nov

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

7. 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

AED 1,064 total

includes taxes & fees

25 Nov - 26 Nov

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Wallingford Center

Jeanette W.

AED 1,094 total

includes taxes & fees

16 Nov - 17 Nov

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

9. New Railside Residents

Wallingford Center

Thomas S.

AED 1,094 total

includes taxes & fees

16 Nov - 17 Nov

10. All New 1BR with tons of Charm

Wallingford Center

Hannah Z.

AED 1,094 total

includes taxes & fees

16 Nov - 17 Nov

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

11. All New Fully Furnished Cozy Studio

Wallingford Center

Rick C.

AED 1,094 total

includes taxes & fees

16 Nov - 17 Nov

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

12. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Igor L.

AED 1,201 total

includes taxes & fees

22 Nov - 23 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.

13. The Sun Filled Cozy Creamery

Plainville

Heather T.

AED 881 total

includes taxes & fees

29 Nov - 30 Nov

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

14. 2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

AED 933 total

includes taxes & fees

14 Nov - 15 Nov

15. Private Apartment in Berlin

Berlin

Shaun L.

AED 992 total

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.

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

Dwight

Stephanie G.

AED 615 total

includes taxes & fees

2 Dec - 3 Dec

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

17. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Lisbeth

AED 481 total

includes taxes & fees

1 Dec - 2 Dec

A view through a window with a clear sky and lush greenery outside.

18. Private Apartment in Southbury 101

Southbury

Marissa G.

AED 870 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Oakville

AED 1,980 total

includes taxes & fees

16 Nov - 17 Nov

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

20. Private Apartment in Southbury 102

Southbury

Debbie P.

AED 870 total

includes taxes & fees

17 Nov - 18 Nov

View all properties

Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

A building with a sign indicating it is an AAA Approved office. There are trees and shrubs in front of the building.

Cheshire Welcome Inn

Cheshire

10/10 Excellent

Benjamin

A Holiday Inn hotel with a covered entrance, multiple floors, and a well-lit facade.

Holiday Inn Cheshire - Southington by IHG

Southington

10/10 Excellent

I liked this hotel. The area was quiet, the staff was professional and the hotel was clean. My only setback was the keycard kept having issues so I had to make trips to front desk. Apart from that, the stay was fine and I would go back. Parking was always available. The hotel sold bkfast and lunches, but also offered free coffee all day. There were food places, including fast foods and diners, that were literally 2‐4 minutes away which was very convenient for the stay.

Constantia

An outdoor kitchen with a grill and a built-in stove, white chairs, and a red door.

Homewood Suites by Hilton Wallingford-Meriden

Wallingford

10/10 Excellent

Anonymous traveler

An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

Homewood Suites by Hilton Southington, CT

Southington

10/10 Excellent

Suzanne Martin

An outdoor patio area with seating, a fire pit, and umbrellas.

Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

10/10 Excellent

Kelly

An outdoor patio area with a fire pit and seating, surrounded by a building with large windows and a parking lot.

Courtyard by Marriott Southington

Southington

10/10 Excellent

Christopher

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

Daniel

A modern bar area with a wooden bar counter, multiple stools, and a variety of liquor bottles.

Courtyard New Haven Wallingford

Wallingford

10/10 Excellent

Michelle

A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

Courtyard by Marriott Waterbury Downtown

Waterbury

10/10 Excellent

Courtney

An outdoor patio area with a fire pit, seating, and a grill.

Residence Inn by Marriott Southington

Southington

10/10 Excellent

Anonymous traveler

A breakfast buffet area with various food options and a bakery section.

Holiday Inn Express Southington by IHG

Southington

10/10 Excellent

Steffani

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

10/10 Excellent

Susan

A stone building with a covered patio area, outdoor seating, and a fire feature.

Homewood Suites by Hilton Orange New Haven

Orange

10/10 Excellent

Meyra

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Matthew

A dimly lit bar with wooden furniture, hanging pendant lights, and a bar counter with a neon sign.

Graduate by Hilton New Haven

Downtown New Haven

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Cheshire Hollow Farm, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers 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 vacation home rentals in Cheshire?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Cheshire vacation home rental. It is located on the beach and has a balcony, a barbecue grill, 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 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 vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.

Cheshire Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire vacation rentals

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

2. Brand New Platform #1

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

4. Newly Remodeled 1-BR Close to Everything yet Very Private

5. All New Studio apartment in center of town

6. Newly Remodeled with deck. Close to town center

7. Fully Furnished 1BR Apartment

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

9. New Railside Residents

10. All New 1BR with tons of Charm

11. All New Fully Furnished Cozy Studio

12. Bear Retreat - 2-bedroom house in Waterbury

13. The Sun Filled Cozy Creamery

14. 2BR Apartment Near Wesleyan 102

15. Private Apartment in Berlin

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

17. Cozy One Bedroom Apartment Centrally Located in Southbury

18. Private Apartment in Southbury 101

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

20. Private Apartment in Southbury 102

Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

Cheshire Welcome Inn

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Cheshire?

What are some of the best vacation home rentals in Cheshire?

What’s there to see and do in Cheshire?

What’s a vacation rental in Cheshire like?