House holiday rentals in Cheshire

4.9 out of 5 average rating, 110 reviews

A spacious living area is presented, featuring a comfortable gray sectional sofa, a wooden coffee table, and a decorative rug. Two green bar stools are positioned at a small counter, and a ceiling fan is mounted above, enhancing the cozy atmosphere of the penthouse apartment.

Home in West Hartford

WeHa Penthouse w/ Private Deck

Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

5 out of 5 average rating, 152 reviews

The kitchen showcases a spacious layout with white cabinetry and modern stainless steel appliances. A large island with seating for several guests is highlighted. Warm lighting from pendant fixtures complements the hardwood floors, while a cozy fireplace is visible in the adjacent living area.

Home in North Haven

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!

4.99 out of 5 average rating, 330 reviews

A cozy living area is presented, featuring a spacious gray sofa and two vibrant orange chairs. A coffee table rests atop a colorful area rug, with natural light filtering in through large windows. Green foliage is visible outside, enhancing the welcoming ambiance.

Home in Fair Haven

Q River House - 2 bdrm, minutes from Yale/Downtown

Q River House: newly remodeled two bedroom home in the historic Fair Haven neighborhood, conveniently located minutes from downtown New Haven and Yale. Take in river views with your morning coffee on the front porch and relax on the large and private back deck. Enjoy one of the city’s many fine restaurants or cook for yourself in the fully appointed modern kitchen. This riverfront home has been lovingly decorated with attention to style and comfort, and features off-street driveway parking.

4.95 out of 5 average rating, 124 reviews

A panoramic view showcases vibrant autumn foliage across rolling hills, with colors ranging from deep reds to bright yellows. The scene is framed by lush greenery in the foreground, while rooftops and distant landscapes are visible in the background under a clear blue sky.

Home in Waterbury

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.

4.94 out of 5 average rating, 123 reviews

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

Connecticut Chalet: Experience Fall in New England

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.

4.99 out of 5 average rating, 207 reviews

A dining area features a long wooden table surrounded by six black chairs. A vintage wooden cabinet stands against the wall, displaying decorative items. Natural light enters through leaded glass windows, creating a warm atmosphere. A patterned rug adds color to the space.

Home in New Haven

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.

4.98 out of 5 average rating, 188 reviews

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

4.96 out of 5 average rating, 121 reviews

The living room features refinished hardwood floors and a neutral colour palette. A spacious sofa and an armchair are arranged around a coffee table, facing a large flat-screen TV mounted above a decorative fireplace. Light streams in through large windows, enhancing the airy feel.

Home in Terryville

Charming 3BR Hill House *Remodeled* w/Arcade

The Lindan Hill House is a perfect AirBnb balance of luxury and value! Stay and play as you enjoy our 5 Star remodeled charming home in Terryville. This quaint and comfy home has everything you need to enjoy your stay including 3 BR with a King/Queen/2 Twin beds with premium bedding. The cozy remodeled basement is perfect for popcorn and movies, dinner and drinks at the bar, and has a game/arcade room with foosball, checkers/chess, and tons of board games! See below for a video tour.

4.99 out of 5 average rating, 135 reviews

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

5 out of 5 average rating, 138 reviews

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.94 out of 5 average rating, 120 reviews

A comfortable living area features a light-colored sofa accompanied by two lamps on side tables. A textured area rug lies beneath a coffee table, while natural light filters through multiple windows, creating a bright and open space. A dining area is visible in the background.

Home in Branford

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

4.93 out of 5 average rating, 201 reviews

The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Popular amenities for house rentals in Cheshire

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 210 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.98 out of 5 average rating, 94 reviews

A spacious living area features large windows that provide natural light and views of the surrounding trees. Comfortable leather furniture includes a sofa and an armchair, arranged around a rustic coffee table on a textured area rug. A potted plant adds a touch of greenery.

Home in Bantam

Hilltop House w/POOL/SPA- HOST & Co.

4.83 out of 5 average rating, 105 reviews

A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.

Home in Milford

Spacious 4 bedroom, oasis with ocean views galore

4.89 out of 5 average rating, 19 reviews

A stone patio is presented, featuring wooden lounge chairs and a table, all framed by expansive glass doors. Beyond the patio, lush greenery stretches across the property, creating a serene and private outdoor space, ideal for relaxation or entertaining.

Home in Redding

Meeker Hill House - Country Escape w/ Heated Pool

4.77 out of 5 average rating, 13 reviews

A circular seating area features white swings surrounding a stone fire pit, which is set within a gravel base. Lush greenery and decorative plants provide a serene backdrop, while a tall fence offers privacy to the gathering space.

Home in Naugatuck

The Oasis in Naugatuck, CT

4.93 out of 5 average rating, 196 reviews

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.9 out of 5 average rating, 119 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

5 out of 5 average rating, 18 reviews

The exterior of the property features well-maintained landscaping with vibrant flowers and greenery. An infinity pool reflects the sky, accompanied by lounge chairs and umbrellas. The house showcases multiple levels with large windows, highlighting the inviting outdoor space.

Home in Newtown

Luxury Escape, Infinity Pool, HotTub, private yard

Weekly house rentals

4.97 out of 5 average rating, 62 reviews

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

Adorable Beach House on LI Sound

5 out of 5 average rating, 19 reviews

An organized kitchen area features sleek white cabinetry, a stainless steel refrigerator, and a gas stove. A single sink is positioned next to the stove, with a tile backsplash in dark tones enhancing the overall design. Natural light fills the space, highlighting the wood floor.

Home in West Haven

1 Bdrm Apt in West Haven

5 out of 5 average rating, 93 reviews

A spacious living room features a large sectional couch adorned with colorful pillows, next to a smaller armchair. Natural light floods through wide windows framed by vibrant curtains. A wooden coffee table sits in the center, with art pieces displayed on the walls and a guitar nearby.

Home in Westville

Westville Schoolhouse by Stephanie and Damian

5 out of 5 average rating, 17 reviews

An open-concept living area features a well-equipped kitchen with modern appliances and an island with seating. Neutral walls and wooden flooring create a warm ambiance. Two pendant lights hang above the kitchen island, illuminating the space and connecting seamlessly to the dining and living areas.

Home in Guilford

Coastal Getaway - walk to town and waterfront

5 out of 5 average rating, 68 reviews

An outdoor seating area is shown with comfortable chairs and a fire pit surrounded by paved stones. A well-maintained lawn and tall evergreen trees provide privacy, while large glass doors lead into the house, inviting natural light into the space.

Home in Prospect Hill

Private 6-Bed House w/ King Bd, Groups & Families

5 out of 5 average rating, 25 reviews

The estate is set on expansive green lawns, framed by mature trees. The picturesque house features a charming combination of traditional architecture and modern details, with expansive verandas and a large outdoor deck providing ample space for relaxation.

Home in East Haddam

Elegant Countryside Estate

4.96 out of 5 average rating, 74 reviews

A welcoming living room features a comfortable couch and two textured armchairs, arranged around a central round coffee table. Natural light filters through large windows, highlighting a cozy atmosphere. A small side table displays a plant and a soft throw blanket.

Home in New Britain

Bright & Private WHOLE HOUSE 4 YOU Near Everything

5 out of 5 average rating, 35 reviews

A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.

Home in Higganum

The Doll House

Private house rentals

4.78 out of 5 average rating, 72 reviews

A cozy living room features a brown sectional sofa with plush cushions and a decorative mirror on the wall. A console piano is positioned next to a large television on a wooden stand. Natural light enters from large windows adorned with sheer curtains, highlighting the warm wood flooring.

Home in Asylum Hill

The Silhouette in Hartford

4.83 out of 5 average rating, 95 reviews

A bright living area features a teal sofa paired with a light gray armchair, accented by a round coffee table at the center. Natural light floods in through large windows, with soft curtains enhancing the serene atmosphere. Art pieces adorn the walls, complementing the hardwood floor.

Home in Bristol

Stylish & Luxurious 3 BDR home with Play Station

4.8 out of 5 average rating, 15 reviews

A single-story blue home is presented, featuring a combination of large windows and a welcoming front entry. Stone steps lead to the door, with landscaped rocks and greenery enhancing the outdoor space.

Home in East Haven

Private Entire Home • Close to New Haven & Shore

5 out of 5 average rating, 3 reviews

A comfortable living area features a green sofa adorned with cushions and a decorative artwork on the wall. Two rattan chairs and a round coffee table are positioned on a patterned area rug. Soft lighting is provided by hanging light fixtures.

Home in New Haven

Apollo’s Haven Entire Unit 6 Min From Yale

4.93 out of 5 average rating, 42 reviews

A light-filled living area features a grey sofa and floral patterned armchair. A television is positioned on a dark wood stand, with a cozy rug anchoring the space. Large windows allow natural light to illuminate the room, complemented by soft white curtains.

Home in Bristol

Walking on Sunshine

4.92 out of 5 average rating, 13 reviews

A spacious outdoor dining area is presented on a red deck, featuring a table set for six, complete with plates and glassware. An umbrella provides shade above, while a grill is positioned nearby. Lush greenery surrounds the deck, enhancing the tranquil setting.

Home in East Haven

Your Home in East Haven

4.78 out of 5 average rating, 36 reviews

A spacious living area is presented with a brown sectional sofa and two decorative pillows. A glass coffee table occupies the center, while natural light pours in through a large window adorned with white trim, offering a view of greenery outside.

Home in Hamden

Cottage Home Retreat