Holiday houses in Cheshire

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Top-rated holiday rentals in Cheshire

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

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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

13 – 20 Aug

$1,375 AUD total

Guest favourite

Home in North Haven

5.0 out of 5 average rating, 123 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

16 – 23 Mar

$9,140 AUD total

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!

15 – 22 Sept

$975 AUD total

Guest favourite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

6 – 13 Sept

$2,088 AUD total

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 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.

28 Mar – 4 Apr

$1,077 AUD total

Guest favourite

Home in New Haven

5.0 out of 5 average rating, 169 reviews

Historic New Haven Home

Our family owned New Haven vacation house is a renovated 1920s Tudor. It's located in a quiet, safe, & beautiful neighborhood, close to downtown and Yale. We've carefully preserved historic aspects we love (ie: art deco tile & leaded glass windows), and combined it with central a/c, USB ports, new appliances, gas fireplace, high speed wifi & more. You’re also welcome to use the small screened in porch, patio with chairs, and the yard. The entire house and driveway is yours when you rent.

24 Apr – 1 May

$2,054 AUD total

Guest favourite

Condo in Middletown

4.97 out of 5 average rating, 101 reviews

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kichen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking, swimming pool. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

23 – 30 Nov

$1,588 AUD total

Guest favourite

Apartment in Southington

4.93 out of 5 average rating, 269 reviews

#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*

You're looking at a new construction Mid-Century Modern inspired In-Law Apartment with private access located in a beautiful, quiet neighborhood right in central CT just 1 minute from I-84. Pet fee $25/night per animal The unit features a large backyard with a patio, fire pit and chairs for your enjoyment. Fires must be approved by host. NOTE: THIS AIRBNB IS ONLY SUITABLE FOR UP TO FOR 4 ADULTS AND 1 CHILD. PLEASE ASK ME IF YOU HAVE ANY QUESTIONS OR CONCERNS.

4 – 11 Aug

$1,641 AUD total

Guest favourite

Apartment in Wallingford

4.86 out of 5 average rating, 22 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.

31 Dec – 7 Jan

$1,056 AUD total

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 184 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.

23 – 30 Jan

$1,503 AUD total

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.

9 – 16 June

$1,117 AUD total

Guest favourite

Guest suite in Hamden

4.96 out of 5 average rating, 713 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.

14 – 21 June

$2,151 AUD total