
House vacation rentals in Cheshire
Find and book unique houses on Airbnb
Top-rated house rentals in Cheshire
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

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.

WaterviewsTakeWedding pics,CollegeTours Yale&Beach
PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

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)

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets
Private lakefront home on Lake Pocotopaug with a fishing dock, kayaks, fire pit, and spectacular sunset views — perfect for family & friend getaways. Welcome to Lakeside Ferns, where you’ll enjoy direct waterfront access and private dock for swimming, fishing, kayaking, canoeing, and boating. Grill dinner, relax in the hammock by the water, and gather around the outdoor fire pit for s’mores under the stars. End each day with breathtaking sunsets over the lake — beautiful in every season.

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.

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.

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Stylish & Luxurious 3 BDR home with Play Station
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with a 2-car garage, ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!

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!

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

Oceanfront Beach House w/ Private Hot Tub
Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.
Popular amenities for Cheshire house rentals
House rentals with a pool

Country getaway - pool, huge yard,

The Getaway-HOST & Co.

Killingworth Estate - Elite Amenities & Finishings

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

Litchfield Modern Farmhouse

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

Long Island home with pool 1 mile from Greenport

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Weekly house rentals

Adorable Beach House on LI Sound

Charming Lakefront Retreat with Spring Lake Views

1,500 sq feet one level ranch completely remodeled

Private Entire Home • Close to New Haven & Shore

Cozy 3BR ! Pet-friendly haven. Book now!

Cottage Home | Near Quinnipiac University

Modern Beach Mood 2!

Historic Village Home Pets Welcome
Private house rentals

Boulder Lake House Retreat

Clean & Quiet Home| Enclosed 3 Season Porch & Deck

Bird's Nest

The Doll House

Cozy Cottage

Entire home in Bristol

Large 2nd floor of duplex in town center

Guest Suite in Southington
Destinations to explore
- Plainview Vacation rentals
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- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Thunder Ridge Ski Area
- Fairfield Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Mount Southington Ski Area
- Yale University Art Gallery
- Sleeping Giant State Park
- Sherwood Island State Park
- Ski Sundown
- Compo Beach
- Orient Beach State Park
- Meschutt Beach
- Ocean Beach
- University of Connecticut
- Stony Brook University




