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Vacation rentals in Connecticut

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Top-rated vacation rentals in Connecticut

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

Guest suite in Cromwell
Spacious downstairs apartment
Spacious guest apartment in basement of home complete with full size kitchen, living space, and bathroom as well as outdoor space access. Private entrance with self check-in through a cellar entrance on the backside of the home. View photos for any concerns regarding a downstairs entrance. Makings for a hot dinner and breakfast are provided in a fully stocked kitchen with all essentials. An alcoholic beverage is offered on your first night. Discounts offered for stays of 5 nights and up.
$79 per night
Treehouse in Willington
Heavenly Treehouse in Countryside w/ Farm Animals
☆ Welcome to the Treehouse at Bluebird Farm in Connecticut ☆ OMG! Explore the countryside at this popular 40-acre sanctuary that has become a favorite among Farms in Connecticut! This is a unique Treehouse in Connecticut. The town of Willington offers: ✔ Hiking Trails ✔ Antiquing ✔ Local Diners ✔ Vineyards & Breweries ✔ National Parks / State Parks ✔ Drive-In Movie Theater We are close drive from: ● UCONN (10 Mins) ● Hartford (25 Mins) ● Boston (1.5 Hours) ● NYC (2.5 Hours)
$179 per night
Guesthouse in Branford
Studio on the shore - Short Beach - Water Views
Our cozy, studio on the shore will make you feel like you’re in a cottage on Nantucket. A beautiful sandy beach awaits you directly across the street. A beautiful park, walking trails and great restaurants all within a 1/2 mile radius. Two bicycles are available to use if you’d like to take a ride into the center of town which has great restaurants, Stony Creek Brewery, train station, shopping and more. An amazing space with a great view and close to everything!
$90 per night

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Other great vacation rentals in Connecticut

Guest suite in Fairfield
Beautiful Private Entrance ensuite in Fairfield
$52 per night
Private room in Middletown
Room for Rent (1)
$47 per night
Guesthouse in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
$128 per night
Rental unit in New Haven
Urban Sanctuary
$84 per night
Cottage in Bridgeport
King Bed Cottage w/ Relaxation Suite & Spa Shower
$107 per night
Private room in Torrington
Suite with private bathroom & entrance & lake
$50 per night
Private room in Waterbury
Private room in a mansion #3
$51 per night
Guesthouse in New Haven
Square 6ix
$72 per night
Guesthouse in Hamden
Cozy 1 bedroom guest/house. We are pet friendly.
$93 per night
Private room in Simsbury
The “Mountain” House Suite
$58 per night
Rental unit in Brookfield
Peaceful apartment on 3.5 acres w/ artist studio.
$101 per night
Private room in New Haven
Maritime Neighborhood Family/Pet Friendly
$59 per night

Your guide to Connecticut

Welcome to Connecticut

Connecticut is more than just New York’s quiet, pastoral neighbor. This small but mighty New England state packs in dozens of quaint towns, flashy promenades, and a heavy dose of pre-Revolutionary War history. Along its southern border, Connecticut is framed by the Long Island Sound, offering pristine sand dunes favored by sunbathers and beachcombers. The southwest pocket of the state is an easy portal to New York City and a convenient base for big-city shopping and dining. The state capital, New Haven, is a brainiac’s dream, home to Yale University, world-class art galleries, museums, and entertainment venues.

Small towns sprinkled throughout the state like Mystic, Wethersfield, and Bristol give travelers a peek into Connecticut's pioneering heritage. More than half of the state is covered by woodland, making it a natural paradise for outdoor activities. Whether you’re exploring the maple- and birch-filled forests of the Eastern Uplands, with their stellar hiking and mountain biking trails, or the rugged Taconic Mountain Range — home to Connecticut’s highest peak, Mount Frissell, and the state’s ski resorts — there’s no shortage of fun to be had in the Constitution State.

When is the best time to stay in a vacation rental in Connecticut?

In autumn, the clear skies and brilliant foliage attract onlookers to Connecticut, making it one of the most popular times of year to book a vacation rental. It’s not just the leaves that will catch your attention. Picking apples from the U-pick orchards, plucking oversized pumpkins from their patches, and getting lost in a corn maze are also popular autumn activities. Spring is great for hiking and biking through the blossoming daffodils and dogwood trees — take note of the many blossom festivals that spring up across the state. Summer means packed beaches and parks along the shoreline, but don’t overlook the many great rural campsites. Just know that the weather will be hot and humid. January is often the coldest month, when the state becomes a haven for skiing and tubing.

What are the top things to do in Connecticut?

Mystic Seaport Museum

Connecticut might be a small state, but it has the largest maritime museum in the country. The Mystic Seaport Museum, in Mystic, is a recreated 19th-century seafaring village celebrating the lives and livelihoods of sailors. Exhibitions range from the craft of woodcarving to popular navigation techniques of the 1800s. Historic boats are available to ride with a captain, and some to pilot yourself, bringing the full experience together.

Gillette Castle State Park

Perched high above the Connecticut River in the city of East Haddam, Gillette Castle State Park offers mesmerizing geologic formations, hiking trails, and a Medieval-style castle. Smooth shale formations and jagged quartz and metamorphic outcroppings might be the first thing to catch your eye upon entering, but the storied stone-and-oak castle, designed by a famed actor and playwright, will warrant a closer look.

Elizabeth Park Rose Garden

Rose-studded archways, perennial-lined paths, and ivy-enshrouded gazebos wind through 100 acres in this formal garden in Hartford. A large hand-dug pond with a stone bridge is a picturesque setting for soaking it all in. The garden’s cafe serves gourmet hot dogs, ice cream, and other snacks during the summer season.