Holiday rentals in Cheshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cheshire

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in New Britain

4.92 out of 5 average rating, 131 reviews

Clean, Quiet and Safe w/Amenities to spare!

This newly renovated in-law apartment (basement) has a private entrance and Ring security protection in the quaint, quiet neighborhood bordering Berlin/New Britain. Come relax, enjoy biking trails, local restaurants and public parks. Renovated with attention to detail, this place has all the comforts of home. Includes two flat screen TVs in bedroom and living room with Fire sticks (cable/movies), two fireplaces and granite vanity & breakfast bar. Working professionals get 10% off long term stays

10–17 Aug

£102 per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

2–9 Aug

£72 per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

17–24 Feb

£80 per night

Guest favourite

Flat in Middletown

4.98 out of 5 average rating, 147 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

4–11 Sept

£128 per night

Guest favourite

Flat in Wallingford

4.86 out of 5 average rating, 21 reviews

Sweet Sparkling Clean Boho 1 bedroom

One bedroom, 3rd story apartment, completely separate, with its own entrance. Comes with a single off street parking space. Centrally located in downtown Wallingford. Close to shops, restaurants and bars. Also within a couple of miles of the Toyota Oakdale Theatre. If you are looking for a place to come and party for the night, this is not a good space for you. This is a quiet building with the landlord on premise. We do welcome fur babies under 50 pounds.

21–28 Aug

£78 per night

Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 183 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

12–19 Mar

£114 per night

Guest favourite

Guest suite in Cheshire

4.94 out of 5 average rating, 31 reviews

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10 and the Merritt Parkway. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. Great place to stay while visiting your family or if you're in the area for business.

14–21 Jul

£90 per night

Guest favourite

Guest suite in Hamden

4.96 out of 5 average rating, 712 reviews

Large Private Studio + Entrance + Bath

Large beautiful secluded studio with a private entry and private bath. Includes comfy queen size bed, futon sofa bed, free wifi, large TV with tons of movies, eat-in table, microwave, mini-fridge, Keurig, closet w/ iron, and your own dedicated room temperature controls. Located in a beautiful, safe, and quiet neighborhood, the studio is attached to a split level house and located in the back on the lower level. It overlooks beautiful woodlands.

16–23 Jun

£159 per night

Superhost

Flat in Plainville

4.82 out of 5 average rating, 125 reviews

#2 *Beautiful 1 BR Apartment - Central CT*

Discover the comfort and convenience of the first floor in a newly built Raised Ranch, strategically located just minutes away from Interstate 84, Lake Compounce and ESPN! Whether you're here for business, pleasure, or to explore the local attractions, this is the perfect place to call home during your stay. The unit boasts a spacious and inviting interior, designed to provide you with all the amenities you need for a relaxing visit.

16–23 Mar

£101 per night

Superhost

Flat in Plainville

4.8 out of 5 average rating, 40 reviews

Studio apartment in Plainville.

This cozy studio apartment is perfect for anyone looking for a quiet, comfortable place to stay. It has been fully renovated, giving it an updated and modern look. Located conveniently close to route 72 and I-84, this spot is perfect for anyone traveling for work or for a couple looking to visit friends or family. It has all the amenities one would need for an extended stay or a short visit, making it the ideal home away from home.

3–10 Dec

£84 per night

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

24–31 Mar

£89 per night

Guest favourite

Home in Cheshire

5.0 out of 5 average rating, 117 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

14–21 Nov

£136 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Cheshire holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cheshire's top sights

Costco Wholesale14 locals recommend

Viron Rondo Osteria5 locals recommend

Blackie's Hot Dog Stand4 locals recommend

Brooksvale Park4 locals recommend

C.J. Sparrow3 locals recommend

Farmington Canal Heritage Trail14 locals recommend

Other great holiday rentals in Cheshire

Guest favourite

Guest suite in Northford

5.0 out of 5 average rating, 11 reviews

Private Bright Studio Retreat with kitchen

8–15 Aug

£92 per night

Guest favourite

Flat in Middlebury

4.98 out of 5 average rating, 64 reviews

Cozy Apartment with Water View of Brook

1–8 Oct

£100 per night

Guest favourite

Home in Southington

4.96 out of 5 average rating, 69 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

6–13 Jul

£297 per night

Guest favourite

Guest house in Wallingford

5.0 out of 5 average rating, 70 reviews

The Garden Loft - A Charming Choate Stay

22–29 Nov

£212 per night

Superhost

Home in Southington

4.87 out of 5 average rating, 15 reviews

Large 2nd floor of duplex in town center

16–23 Sept

£134 per night

Superhost

Flat in Meriden

5.0 out of 5 average rating, 3 reviews

Hillside Retreat

26 Jun – 3 Jul

£140 per night

Guest favourite

Guest suite in Durham

4.84 out of 5 average rating, 19 reviews

Spacious Studio in quiet neighborhood.

29 Jun – 6 Jul

£110 per night

Guest favourite

Flat in Hamden

4.86 out of 5 average rating, 14 reviews

Welcoming & Clean Condo near Hamden Shopping

16–23 Nov

£106 per night

Show all

Quick stats about holiday rentals in Cheshire

Total rentals	20 properties
Wifi availability	20 properties include access to wifi
Rentals with dedicated workspaces	10 properties have a dedicated workspace
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	550 reviews
Nightly prices starting at	£24 before taxes and fees

Holiday rentals in Cheshire

Top-rated holiday rentals in Cheshire

Guest suite in New Britain

Guest suite in Watertown

Guest suite in Wallingford

Flat in Middletown

Flat in Wallingford

Flat in Brookfield

Guest suite in Cheshire

Guest suite in Hamden

Flat in Plainville

Flat in Plainville

Guest suite in Morris

Home in Cheshire

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Cheshire holiday rentals

Stay near Cheshire's top sights

Other great holiday rentals in Cheshire

Guest suite in Northford

Flat in Middlebury

Home in Southington

Guest house in Wallingford

Home in Southington

Flat in Meriden

Guest suite in Durham

Flat in Hamden

Quick stats about holiday rentals in Cheshire

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore