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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.

Enjoy the View in a Quiet and Relaxed Apartment
SUPERHOST
Entire guest suite · 4 guests · 1 bed · 1 bath
Enjoy the View in a Quiet and Relaxed ApartmentA quiet breeze carrying the sound of wind chimes will greet you at this easy to reach, centrally located apartment. Sit on the patio as you enjoy the natural vista or the fire pit. A relaxed and charming place to kick back and rest, or go on daily hikes on one of the many nearby hiking trails. This lovely and quiet corner of Northwest Connecticut will give you the relaxation and location to make your trip enjoyable. Close to many wonderful hiking spots, breweries, wineries, and antiquing.
Unique, fun riverfront cottage
SUPERHOST
Entire residential home · 4 guests · 4 beds · 1 bath
Unique, fun riverfront cottageOur guesthouse is on the Connecticut River in the treasured small town of Chester, half-way between New York and Boston – a little over two hours from each city and 45 minutes from New Haven and Hartford. The cottage features a wide porch, private front yard overlooking the river; a living room with a couch that pulls out to sleeps two comfortably, a dining area and kitchen at one end with a dishwasher. There's a bedroom with a queen-sized bed and a good-sized bathroom with tub and shower. A loft has two single beds, most suitable for children over 10 and younger adults. The house, on our four-acre property, is private and quiet and about two miles from the center of the village which is well-appointed with wonderful restaurants, a professional theater, galleries and one-of-a-kind shops. There is endless hiking and kayaking possibilities with a boat launch ramp adjacent to the property. Theater, music and a variety of activities and things to do are all close by. The cottage is $130 a night; $700 a week or $2500 a month. During January and February, March and April the price is $110 a night; $660 a week and $1700 a month. We’d love to have you stay.
Insta-worthy * Couples Retreat
SUPERHOST
Entire bungalow · 5 guests · 4 beds · 1 bath
Insta-worthy * Couples RetreatOur 1940's, completely remodeled and updated bungalow style cottage is full of a long line of Hawks Nest Beach history and has been transformed into a beachy oasis.

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Other great vacation rentals in Connecticut

SUPERHOST
  1. Entire cottage
  2. Old Lyme
2 bedroom full cottage small weekly rental Getaway
ﺩ.ﺇ323 per night
SUPERHOST
  1. Entire rental unit
  2. Milford
Water front studio apartment with fireplace.
ﺩ.ﺇ454 per night
SUPERHOST
  1. Entire guesthouse
  2. Cornwall
Cottage at Furnace Brook
ﺩ.ﺇ300 per night
SUPERHOST
  1. Entire guesthouse
  2. Granby
Windy Top Cottage ~ A Romantic "European" Getaway
ﺩ.ﺇ496 per night
  1. Entire rental unit
  2. New London
Private Studio Apt in Restored Historic Mansion
ﺩ.ﺇ209 per night
SUPERHOST
  1. Entire rental unit
  2. New Haven
Urban Sanctuary
ﺩ.ﺇ331 per night
SUPERHOST
  1. Entire guest suite
  2. Sherman
Scenic country retreat w/views, nearby hiking/ski
ﺩ.ﺇ380 per night
SUPERHOST
  1. Entire cottage
  2. East Lyme
★Cozy & Bright Coastal Cottage - Private Beach★
ﺩ.ﺇ455 per night
SUPERHOST
  1. Entire cottage
  2. Ledyard
Waterfront cottage overhanging the water!
ﺩ.ﺇ372 per night
SUPERHOST
  1. Entire rental unit
  2. Southington
#19 *CozySpace* A tiny place to call home*
ﺩ.ﺇ272 per night
  1. Entire rental unit
  2. New London
Private Studio Apartment in Historic Mansion
ﺩ.ﺇ165 per night
  1. Entire guest suite
  2. Fairfield
Beautiful Private Entrance ensuite in Fairfield
ﺩ.ﺇ213 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.


How do I get around Connecticut?

Connecticut is connected to the rest of the country by nearly every mode of transportation — from private helipads to classic commuter trains. While many people from out of state fly into New York City to get to Connecticut, Bradley International Airport (BDL) in Windsor-Locks offers international flights, and Groton-New London Airport (GON) and Tweed-New Haven Regional Airport (HVN) roll out domestic and regional service. On the ground, local highways and country roads make it a breeze to explore every corner of the state by car. Local commuter and Amtrak trains link Connecticut with Washington D.C., New York, and Maine. Around a half-dozen ferry terminals provide an alternative mode of transportation while cruising Connecticut’s scenic shoreline.


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 visit. 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.