Connecticut vacation rentals

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Top-rated vacation rentals in Connecticut

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

Guest favorite
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!
Aug 28 – Sep 4
$175 per night
4.97 out of 5 average rating, 505 reviews
Guest favorite
Guesthouse in Stonington
True Artist Loft, 5 minutes to downtown Mystic
The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.
Aug 22 – 29
$200 per night
4.98 out of 5 average rating, 216 reviews
Guest favorite
Guest suite in Wallingford
Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.
Jan 8 – 15
$73 per night
5.0 out of 5 average rating, 492 reviews

Popular amenities for Connecticut vacation rentals

Connecticut waterfront vacation rentals

Guest favorite
Home in Stamford
Midcentury Modern ZenHouse Sculptor Studio
Aug 31 – Sep 7
$482 per night
4.97 out of 5 average rating, 216 reviews
Guest favorite
Cabin in Sherman
The Cove Cabin
Nov 14 – 21
$485 per night
4.97 out of 5 average rating, 303 reviews
Guest favorite
Cottage in Voluntown
Lakeside Cottage in the Forest
Nov 23 – 30
$136 per night
4.95 out of 5 average rating, 179 reviews
Guest favorite
Bungalow in Old Lyme
Pet Friendly Bungalow!!!
Feb 3 – 10
$166 per night
4.93 out of 5 average rating, 247 reviews
Guest favorite
Cottage in Guilford
Luxury cottage by the sea with hot tub and pool
Jan 2 – 9
$321 per night
4.96 out of 5 average rating, 156 reviews
Guest favorite
Home in Lyme
“The Answer” Tidal River-Kayaks Fire pit Fireplace
Sep 18 – 25
$297 per night
4.97 out of 5 average rating, 184 reviews
Guest favorite
Home in Cornwall
Secluded modern forest cabin with private brook
Jul 10 – 17
$201 per night
4.92 out of 5 average rating, 222 reviews
Guest favorite
Cottage in Watertown
Lakefront Cottage with Private Dock in CT
Jun 22 – 29
$157 per night
4.81 out of 5 average rating, 129 reviews
Guest favorite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
Dec 19 – 26
$184 per night
4.98 out of 5 average rating, 225 reviews
Guest favorite
Cottage in Ledyard
Waterfront cottage overhanging the water!
Nov 8 – 15
$182 per night
4.91 out of 5 average rating, 139 reviews
Guest favorite
Tiny home in Norwich
Water Forest Retreat-Hikers Haven
Aug 19 – 26
$135 per night
5.0 out of 5 average rating, 505 reviews
Guest favorite
Cabin in North Stonington
Come unplug in the woods 15 mins from Mystic
Aug 10 – 17
$164 per night
4.95 out of 5 average rating, 146 reviews

Connecticut fishing vacation rentals

Guest favorite
Guesthouse in Southbury
Charming Guest Cottage with Modern Amenities
Aug 3 – 10
$135 per night
4.93 out of 5 average rating, 265 reviews
Guest favorite
Cottage in Middlefield
Lake Beseck cottage
Sep 5 – 12
$106 per night
4.93 out of 5 average rating, 228 reviews
Guest favorite
Apartment in East Lyme
Brand New Direct Lakefront - Panoramic Sunsets
Jun 29 – Jul 6
$454 per night
4.97 out of 5 average rating, 161 reviews
Guest favorite
Home in North Stonington
The Perch
Nov 15 – 22
$334 per night
4.98 out of 5 average rating, 103 reviews
Guest favorite
Apartment in New Haven
Fair Haven Heights Entire 1 Bedroom Apartment
Sep 11 – 18
$99 per night
4.89 out of 5 average rating, 465 reviews
Guest favorite
Home in Vernon
Luxe Bolton Lake!
May 29 – Jun 5
$509 per night
4.99 out of 5 average rating, 113 reviews
Guest favorite
Cottage in Killingly
Lake front cottage
Oct 23 – 30
$140 per night
4.94 out of 5 average rating, 419 reviews
Guest favorite
Apartment in Deep River
Loft apartment, deck and great water view
Jan 2 – 9
$101 per night
4.82 out of 5 average rating, 170 reviews
Superhost
Cabin in Windham
Secluded Cabin on Golden Pond
May 7 – 14
$142 per night
4.85 out of 5 average rating, 117 reviews
Guest favorite
Guest suite in Thompson
Meadowside: Perfect Location w/ Endless Recreation
Aug 29 – Sep 5
$142 per night
4.98 out of 5 average rating, 110 reviews
Guest favorite
Home in Danbury
Candlewood Lakefront Retreat
Apr 24 – May 1
$375 per night
4.87 out of 5 average rating, 114 reviews
Superhost
Home in Woodstock
Lakeside Retreat on 4 Stunning Acres + Hot Tub
Apr 2 – 9
$439 per night
4.92 out of 5 average rating, 132 reviews

Connecticut house rentals

Guest favorite
Home in Milford
The Daydreamer -Walk to Walnut Beach, Pet Friendly
Nov 24 – Dec 1
$200 per night
4.99 out of 5 average rating, 220 reviews
Guest favorite
Home in Old Lyme
Modern Farmhouse with Hot Tub in Old Lyme, CT
Dec 8 – 15
$347 per night
4.96 out of 5 average rating, 119 reviews
Guest favorite
Home in Wilton
Mid Century Modern Cottage
Jun 29 – Jul 6
$135 per night
4.94 out of 5 average rating, 157 reviews
Guest favorite
Home in North Haven
Luxury Stay in Expansive Historical Home
Sep 12 – 19
$752 per night
5.0 out of 5 average rating, 122 reviews
Guest favorite
Home in Old Lyme
Modern Luxurious CT Country Home
Feb 16 – 23
$356 per night
4.94 out of 5 average rating, 256 reviews
Guest favorite
Home in Westbrook
Family-Friendly Cottage by The Shore
May 11 – 18
$182 per night
4.86 out of 5 average rating, 130 reviews
Guest favorite
Home in Fairfield
Luxurious Barn With New England Charm
Apr 23 – 30
$192 per night
4.96 out of 5 average rating, 287 reviews
Guest favorite
Home in Cheshire
Pool House
Nov 1 – 8
$126 per night
5.0 out of 5 average rating, 116 reviews
Guest favorite
Home in Stamford
STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
Apr 28 – May 5
$85 per night
4.98 out of 5 average rating, 130 reviews
Guest favorite
Home in Litchfield
Stunning Views, Bucolic Bliss in 1790s Farmhouse
Apr 13 – 20
$383 per night
4.93 out of 5 average rating, 162 reviews
Guest favorite
Home in Branford
Shoreline Treasure in Lanphiers Cove
May 7 – 14
$229 per night
4.98 out of 5 average rating, 124 reviews
Guest favorite
Home in Bristol
Cozy Family Home - Kid & Pet Friendly
Feb 19 – 26
$119 per night
4.92 out of 5 average rating, 101 reviews

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