Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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

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Superhost
Apartment in Southington
5 out of 5 average rating, 9 reviews

Betty’s Brickhouse-ask about shorter stays

This is a very cozy one bedroom (2nd floor)- the bedroom has a 33” TV and fanimation fan/light -comfortable and inviting living room with 50” TV with WiFi. Great new kitchen space with ss appliances including a “knock knock” refrigerator, stove, toaster, microwave, dishwasher, coffee maker, pots and pans and even a washer and dryer. The bath is simply spectacular -all new and sparkling clean with plenty of towels, etc. We also have the convenience of keyless entry. Please note-Must climb stairs

Top guest favorite
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, 191 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!

Guest favorite
A modern kitchen features sleek cabinetry and a spacious island with a stone base. Three bar stools are positioned at the island, next to stylish pendant lights. A stainless steel refrigerator and a microwave are visible, along with various kitchen essentials arranged thoughtfully on the counter.
Guest suite in Wolcott
4.89 out of 5 average rating, 80 reviews

Modern cozy, pet friendly

Kick back and relax in this calm, stylish space. This is a full finished apartment with a private entrance full bathroom full one bedroom full kitchen, second bed-sleeper sofa in the living room. This is a private property we live upstairs. very safe clean neighborhood. Property sits on a 3.5 acres. From parking to the entrance is a short walk thru the grass yard. protect you trip in case of unexpected events that may require cancellation. Travel insurance can be purchased thru Airbnb .

Top guest favorite
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
4.94 out of 5 average rating, 125 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 favorite
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.
Guesthouse in Wallingford
5 out of 5 average rating, 144 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 favorite
A serene lakeside view features a well-maintained lawn leading to calm waters. Two comfortable yellow chairs are positioned on the grass, offering a perfect spot for relaxation. Trees frame the setting, while distant homes can be seen along the shoreline, enhancing the peaceful ambiance.
Home in Wolcott
4.91 out of 5 average rating, 33 reviews

Cozy Waterfront Lake House: 5 mins from ski slopes

Relax at this peaceful 1BR lakefront retreat—perfect for couples or small families. Summer: Enjoy kayaking, swimming, grilling, outdoor dining, and fire pit s’mores. Off-season stays offer crisp hikes, lake views, fires, nearby skiing at Mt. Southington (5 mins), and family fun at Lake Compounce. Sleeping arrangements include a queen size bed in a Bedroom, a pullout sofa bed and a queen sized blow up mattress. Self check-in, fresh linens, and a welcoming vibe await.

Top guest favorite
A spacious living area features a plush sectional sofa adorned with decorative pillows. A rectangular coffee table sits in the center, accompanied by a small potted plant. Natural light enters through a window, while a private entrance door is visible in the background.
Guesthouse in Southington
4.96 out of 5 average rating, 25 reviews

Cozy Private Guest Suite

Welcome to your perfect home-away-from-home in Southington, CT! This private basement guest suite offers a cozy, quiet escape with everything you need for a comfortable stay. Whether you're visiting for business, or just passing through, you'll enjoy a peaceful space with a private entrance, living area, and essential amenities. Free parking on premises Located in a quiet neighborhood just minutes from local restaurants, walking trails, and easy access to I-84

Top guest favorite
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.
Apartment in Prospect Hill
5 out of 5 average rating, 171 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 favorite
An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.
Guest suite in Wallingford
5 out of 5 average rating, 637 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. I am not responsible for wifi.

Guest favorite
Apartment in Wallingford
4.94 out of 5 average rating, 102 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. No pets.

Guest favorite
A spacious living area features a dual-sofa arrangement with decorative cushions. A wooden desk is positioned nearby, illuminated by a lamp. Natural light streams through multiple windows adorned with red curtains, enhancing the well-lit ambiance. Decorative artwork hangs on the walls.
Apartment in Wallingford
4.93 out of 5 average rating, 15 reviews

Seasons Hospitality LibraryLuxe 1BR

Welcome to Platform 9 at "The Station" Once an old silver factory now converted into a fully furnished 1-bedroom apartment, where the echoes of the past harmonize with the comforts of the present. This brand new apartment includes all utilities, free off street parking, free washer and dryers and all linens. Located in the center of town and walking distance to shopping, restaurants and all what Wallingford has to offer.

Top guest favorite
A cozy bedroom area features a spacious bed with soft linens and decorative pillows. A small white side table and a round light fixture are present. A comfortable white sofa and a modern black chair are arranged in the relaxation area, alongside a neutral patterned rug.
Apartment in Edgewood
4.97 out of 5 average rating, 79 reviews

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.

Popular amenities for Cheshire vacation rentals

Frequently Asked Questions

  • 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.

  • 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.

  • What are the most popular amenities for House Rentals in Cheshire?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

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

    Experience the best of Cheshire with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

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