Skip to content

Connecticut vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Connecticut

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

Apartment in Milford
Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!
$149 per night
Apartment in Brookfield
Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.
$121 per night
Guest suite in Wallingford
Wintergreen Gardens @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker and 40" HDTV with Amazon Prime Video, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, enjoy a book or a hot cup of coffee. Close to town and all the food you could possibly want! Short drive to 4 vineyards, Oakdale Theater and the train station.
$81 per night

Connecticut summer vacation rentals

Guesthouse in Guilford
Get Back to Nature at a Modern Wood Clad Getaway
$200 per night
Guesthouse in Stonington
True Artist Loft, 5 minutes to downtown Mystic
$202 per night
Cottage in Milford
Winter Sale! Cozy Modern Rustic Cottage-Yard-W/D
$99 per night
Home in Branford
Adorable Beach House on the Long Island Sound
$164 per night
Guesthouse in New Haven
Square 6ix
$72 per night
Guest suite in Bethlehem
Breezy Crest private & restful w/antique charm
$132 per night
Home in Preston
Entire House Magical Waterfront Getaway
$160 per night
Home in Milford
The Daydreamer -Walk to Walnut Beach, Pet Friendly
$121 per night
Apartment in Ashford
Enjoy a Farm Stay without the Work
$79 per night
Cottage in Groton
$165 per night
Loft in New Haven
Full loft apartment near Omni Hotel
$107 per night
Home in East Haven
Beach Cottage by the Sea
$124 per night

Connecticut beach vacation rentals

Guest suite in New Haven
Cozy cottage in historic neighborhood
$129 per night
Guesthouse in Mystic
Gorgeous Waterfront Getaway
$156 per night
Cottage in East Lyme
Your Nest Near The Beach
$155 per night
Cottage in Guilford
Luxury cottage by the sea with hot tub and pool
$289 per night
Apartment in Stamford
Seaside Serenity: 1BR Getaway.
$101 per night
Cottage in Old Lyme
Private Beach Cottage
$68 per night
Apartment in Groton
⭐ Modern Studio in Heart of Downtown Mystic
$89 per night
Apartment in West Haven
! ! ! entire apartment close to the beach ! !
$91 per night
Cottage in Waterford
Coastal Cottage Private Studio
$160 per night
Guesthouse in Groton
Quiet studio with sleeping loft and deck
$94 per night
Guesthouse in Fairfield
Southport, CT across from BEACH
$232 per night
Guest suite in Greenwich
Charming Greenwich studio, 0.2 miles from train
$122 per night

Connecticut home rentals

Home in Milford
Designer Beach Retreat on Exclusive Cedar Beach
$268 per night
Home in Litchfield
Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ
$75 per night
Home in Cornwall
Secluded modern forest cabin with private brook
$196 per night
Home in Lyme
“The Answer” Tidal River-Kayaks Fire pit Fireplace
$207 per night
Home in Wilton
Mid Century Modern Cottage
$135 per night
Home in Preston
New Lake Front Home w/ Game Room & Stunning Views
$286 per night
Home in Cheshire
Pool House
$140 per night
Home in New Haven
Q River House - 2 bdrm, minutes from Yale/Downtown
$140 per night
Home in Manchester
Paradise On The Hill Luxury Apartment.
$83 per night
Home in Newtown
Private and Serene home close to I-84 and shopping
$150 per night
Home in Stonington
Eco Friendly 1700s home! 0.3 miles to Westerly RI!
$155 per night
Home in Milford
The Beach House!
$245 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.

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.

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.

Destinations to explore