Holiday rentals 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
Home in Waterbury
4.96 out of 5 average rating, 143 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom 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 (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

Top guest favourite
A dining area features a wooden table surrounded by dark chairs, set with blue and white plates. Large windows allow natural light and provide an expansive view of the lake, where boats can be seen in the distance.
Cottage in Middlefield
4.97 out of 5 average rating, 111 reviews

Anchors' Away-

Welcome to your private lakefront sanctuary. Have the chance to make memories whether it is by fishing on either of the two docks? or the chance to kayak to explore the lake. Completely renovated with comfort and style in mind, this waterfront getaway offers panoramic lake views and direct water access. Start your mornings with coffee on one of the two private docks watching the sunrise. Unwind each evening on the patio all decked out with restful seating and a chance to watch the fireflys.

Top guest favourite
A studio layout features a queen-sized bed with neutral bedding, situated under a sloped ceiling with recessed lighting. A small dining table and two chairs are positioned near a closet. A Smart TV is mounted on the wall, complementing the wooden flooring.
Guest suite in Cheshire
4.94 out of 5 average rating, 216 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
A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.
Home in Southington
4.93 out of 5 average rating, 135 reviews

Connecticut Chalet: Winter Nights by the Fire

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
A well-lit bedroom features a spacious bed, accentuated by a floral wallpaper backdrop. A large skylight and a window allow natural light to fill the room. A woven bench sits at the foot of the bed, complemented by a green plant near the window.
Flat in Prospect Hill
4.98 out of 5 average rating, 184 reviews

Skylight: Cozy 2 BR, Close to Yale & Downtown NHV

Huge skylights cast light into every room of this stunning two bedroom apartment. Located within walking distance of Yale's campus, this is the perfect place to spend a weekend, month, or entire semester. Skylight was recently renovated and has central air, washer/dryer, fast wifi, a large kitchen, and easy parking. Set on a quiet tree-lined street, this is the perfect place for your New Haven visit. For more space, please look at our listings Haven and The Blue Bird in the same house!

Top guest favourite
The exterior of a bright red carriage house is surrounded by lush gardens filled with various flowers and greenery. Two large windows and a white door are visible, adding charm to the traditional New England design. A well-maintained lawn complements the vibrant landscape.
Guest house in Wallingford
5 out of 5 average rating, 151 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
The exterior of the two-story home is showcased, featuring a light-colored facade with multiple gabled roofs. A well-maintained lawn surrounds the house, accented by blooming shrubs. A paved driveway leads to a two-car garage, and trees provide a natural backdrop.
Flat in Waterbury
4.99 out of 5 average rating, 120 reviews

Everything you need! Full Apartment!

Bright and private, this 2nd-floor apartment has everything you need! Features a full kitchen, laundry, and easy highway access. Located on a quiet cul-de-sac near great local bars and restaurants. Enjoy Wi-Fi, Netflix, Prime, and Hulu. Dedicated parking is behind the left garage. FYI: I host card games in the garage below until 11:30 PM, but my guests won't use the driveway. Plus, feel free to use the grill and small patio behind the garage! A cozy, homey retreat for your stay.

Top guest favourite
A spacious living area features a large sectional sofa adorned with red cushions, complemented by a coffee table and side tables. Bright light floods the room through the sliding glass doors, opening to the outdoor deck. A staircase leads to a lofted area, enhancing the open feel.
Flat in Guilford
4.96 out of 5 average rating, 100 reviews

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck, take a dip in the crystal-clear waters, or explore nearby nature trails. A lofted office space with l-shaped desk invites both creativity and productivity. Your lakeside escape awaits! NO CLEANING FEE!

Top guest favourite
An aerial view captures a sprawling farm landscape at sunset, with the sun dipping behind rolling hills. The guest house, white with a gray roof, is surrounded by green fields and lush vegetation, creating a serene atmosphere.
Farm stay in New Milford
5 out of 5 average rating, 130 reviews

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers that is sold at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, and chickens. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Guest favourite
A spacious living area is furnished with a cozy red reclining couch facing a flat-screen TV. A colorful area rug enhances the space, complemented by two pieces of wall art. A small fridge and a decorative cabinet are present, alongside a door leading outside.
Flat in Wallingford
4.78 out of 5 average rating, 120 reviews

Wallingford Getaway

ENJOY DAILY CONTINENTAL BREAKFAST INCLUDED WITH minimum two night stay. Experience a cozy stay in our spacious 1300 square foot unit with included breakfast. Choose from muffins, bagels, bars and yogurt. Enjoy a relaxing afternoon with a cup of Java from your own Keurig. This unit features a comfy red electric red reclining couches and a flat screen TV. The kitchen area is equipped with a toaster microwave convection oven and fridge.

Top guest favourite
A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.
Flat in Prospect Hill
5 out of 5 average rating, 186 reviews

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

Top guest favourite
The welcoming exterior of a classic two-story home is showcased, featuring dark siding and white shutters. A well-maintained pathway leads to the entrance, illuminated by a lamp post. Rocking chairs are visible on the porch, with light spilling from the windows, suggesting a cozy atmosphere.
Flat in Wallingford
4.96 out of 5 average rating, 404 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

Popular amenities for Cheshire holiday rentals

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Cheshire?

    Experience the best of Cheshire with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Cheshire?

    Yes! Work meets play with ease at over 10 vacation rentals in Cheshire featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Cheshire have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Cheshire. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheshire have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Cheshire. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheshire have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Cheshire. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cheshire have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Cheshire. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Cheshire

  • Total holiday rentals

    Explore 30 holiday rentals in Cheshire

  • Nightly prices starting at

    Cheshire holiday rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 660 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Cheshire holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheshire rentals

  • 4.8 Average rating

    Cheshire stays are highly rated by guests – averaging 4.8 out of 5!

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