
House holiday rentals in Cheshire
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Top-rated house rentals in Cheshire
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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.

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Bright & Private WHOLE HOUSE 4 YOU Near Everything
Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

Connecticut Chalet: Summer Retreat on 5 Acres
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.

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!

Westville Schoolhouse by Stephanie and Damian
The beautiful "School House" sits in the heart of Westville, New Haven's most artsy and eclectic neighborhood. The "School House" is a 15 minute walk to the Westville Concert bowl, and the Yale Football stadium for an easy commute to a concert or game. Just a one minute walk to the center of Westville you will find Lotta's artist studio, Bella's restaurant, RAWA, Pistachio Coffee and Manjares Tapas & Wine, as well as the famous Camacho Garage restaurant amongst other attractions.

Westshore Luxury
Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

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

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.

The Cottage at Cedar Spring Farm
Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!
Popular amenities for house rentals in Cheshire
House rentals with a pool

15 acres! * Pine Pond at Devils Hopyard State Park

3.5 Acres of Relaxation, Pool, & Cozy Charm

Private Oasis W/Stunning Vinyard and Pool Views

Breathtaking home with unforgettable views & pool!

The Getaway-HOST & Co.

Hilltop House/HOST &Co.

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Mountaintop Nirvana: Lake, Hot Tub, Pool Table
Weekly house rentals

The Gait House at High Gait Farm

Adorable Beach House on LI Sound

Quarry House: Mid-Century Modern

Hot Tub Getaway | Game Room + Fireplace

Private Entire Home • Close to New Haven & Shore

Mulberry Seaside Cottage

The Farmhouse Stay

Private Barn Retreat Nestled In Nature
Private house rentals

Gorgeous Luxury INDOOR POOL home

The Jewel of The Cove - Historic Coastal Retreat

Cozy Pet Friendly Lake Cottage!

Fortune Retreat

Brand new Waterfront house | Dock | Hot Tub& Kayak

Backyard Tiny House in the Woods

Field of Dreams Hot Tub - Fire Pit Retreat

Charming 1875 Retreat - Walk to Village
Quick stats about house rentals in Cheshire

Total holiday rentals
Explore 10 holiday rentals in Cheshire

Nightly prices starting at
Cheshire holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 270 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Fairfield Beach
- Mohegan Sun
- Ocean Beach Park
- Foxwoods Resort Casino
- Sunken Meadow State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Sherwood Island State Park
- Compo Beach
- Ski Sundown
- Orient Beach State Park
- Mount Southington Ski Area
- Ocean Beach
- University of Connecticut
- Millbrook Vineyards & Winery
- Meschutt Beach





