Vacation rentals in Cheshire

Find and book unique accommodations on Airbnb

Top-rated vacation 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

Apartment in Meriden

4.93 out of 5 average rating, 27 reviews

Hillside Retreat

Welcome to our little hillside hollow, tucked away on the east side of Meriden. I am a gardener and enjoy cultivating a wildlife habitat on our property. The retreat has been carefully designed for tranquility. It features a galley kitchen with a reading nook, a tiled bathroom, and a sweet bedroom with a small private deck overlooking the back yard, trees, and walking path. While the retreat feels rural, it is convenient to downtown, and to the noted hiking trails in the center of the state.

Guest favourite

Apartment in North Haven

4.89 out of 5 average rating, 44 reviews

Charming Dog Friendly Suite On Scenic Property

This home features a private entrance with access to large yard, deck and propane grill. The spacious apartment has a cozy living space with a pool table and entertainment seperate from bedroom and bathroom. Close easy access to I-91 and the Merrit Parkway. Tucked away in an affluent enclave of Mt. Carmel minutes from Quinnipiac University and Sleeping Giant state park. Great for someone who wants to explore the many natural beauties and attractions the area has to offer, or a peaceful getaway.

Top guest favourite

Guest suite in Cheshire

4.92 out of 5 average rating, 144 reviews

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. 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. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Top guest favourite

Home in Waterbury

4.93 out of 5 average rating, 75 reviews

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

Guest favourite

Home in Waterbury

4.95 out of 5 average rating, 117 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom newly updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (month of July). Wi-Fi/cable, central AC/hot air, washer/dryer, and grill are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey table) are provided. This house is truly relaxing and will feel like home.

Guest favourite

Home in Southington

4.95 out of 5 average rating, 118 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Top guest favourite

Guesthouse in Wallingford

5 out of 5 average rating, 119 reviews

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Top guest favourite

Guesthouse in Portland

5 out of 5 average rating, 205 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Top guest favourite

Apartment in New Britain

4.95 out of 5 average rating, 194 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Guest favourite

Apartment in Downtown New Haven

4.92 out of 5 average rating, 226 reviews

Stay @ the Roost on Mansfield in the heart of Yale

The Roost on Mansfield is a cozy and comfortable two bedroom apartment located in the heart of campus right across from the Yale Hockey Rink. The Roost has lots of sunlight, is fully furnished, has great amenities- free secure off-street parking, beddings, great cooking gear, everything you need as a guest. The building has exterior cameras, security monitoring and is equipped with digital locks for flexible check-in.

Top guest favourite

Guest suite in Wallingford

5 out of 5 average rating, 593 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private 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.

Top guest favourite

Apartment in Wallingford

4.97 out of 5 average rating, 379 reviews

Spacious in-law apartment steps from Choate

Private apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio