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
Treehouse in Thompson
The Tree House at Underhill Hollow
The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.
Mar 25 – Apr 1
$106 per night
4.96 out of 5 average rating, 327 reviews
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
Cottage in Waterford
Classic CT Cottage w/ Trail by Harkness Park/Ocean
Tastefully appointed! A quaint cottage in a forest setting on 6 acres bordering Harkness State Park. A peaceful & serene setting where you can hear nature by day and the lighthouse sound signal at night. The cottage is fully equipped & very comfortable for your stay. The Waterford beach is a short drive away...less than 2 miles through the forest...as are beautiful hikes along the coast. Centrally located near Historic Mystic, Niantic, Conn College, US Coast Guard Academy & the US Naval Base.
Apr 13 – 20
$131 per night
4.99 out of 5 average rating, 102 reviews

Popular amenities for Connecticut vacation rentals

Connecticut waterfront vacation rentals

Guest favorite
Home in Branford
Adorable Beach House on the Long Island Sound
May 5 – 10
$176 per night
4.91 out of 5 average rating, 359 reviews
Guest favorite
Tiny home in Norwich
Water Forest Retreat-Hikers Haven
Apr 23 – 30
$135 per night
5.0 out of 5 average rating, 505 reviews
Guest favorite
Home in Preston
New Lake Front Home w/ Game Room & Stunning Views
Dec 21 – 28
$350 per night
5.0 out of 5 average rating, 116 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!!!
Sep 15 – 22
$166 per night
4.93 out of 5 average rating, 247 reviews
Guest favorite
Home in Milford
Designer Beach Retreat on Exclusive Cedar Beach
Oct 7 – 14
$273 per night
4.98 out of 5 average rating, 144 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
Guest favorite
Home in Stamford
Midcentury Modern ZenHouse Sculptor Studio
Jun 5 – 12
$482 per night
4.97 out of 5 average rating, 216 reviews
Guest favorite
Apartment in New Haven
Fair Haven Heights Entire 1 Bedroom Apartment
Jun 3 – 10
$99 per night
4.89 out of 5 average rating, 465 reviews
Guest favorite
Cottage in Guilford
Luxury cottage by the sea with hot tub and pool
Feb 4 – 11
$293 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
Cottage in Watertown
Lakefront Cottage with Private Dock in CT
May 7 – 14
$157 per night
4.81 out of 5 average rating, 129 reviews

Connecticut fishing vacation rentals

Guest favorite
Cottage in Middlefield
Lake Beseck cottage
Sep 12 – 19
$106 per night
4.93 out of 5 average rating, 228 reviews
Guest favorite
Guesthouse in Southbury
Charming Guest Cottage with Modern Amenities
May 4 – 11
$135 per night
4.93 out of 5 average rating, 265 reviews
Guest favorite
Cabin in New Fairfield
The Little Lake Cabin— hot tub, fire pit, & kayaks
Oct 16 – 23
$316 per night
4.98 out of 5 average rating, 251 reviews
Guest favorite
Apartment in Deep River
Loft apartment, deck and great water view
Mar 30 – Apr 6
$98 per night
4.82 out of 5 average rating, 170 reviews
Guest favorite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
Dec 20 – 27
$184 per night
4.98 out of 5 average rating, 225 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
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 Vernon
Luxe Bolton Lake!
May 30 – Jun 6
$515 per night
4.99 out of 5 average rating, 113 reviews
Guest favorite
Home in North Stonington
The Perch
Nov 15 – 22
$334 per night
4.98 out of 5 average rating, 103 reviews
Superhost
Cabin in Windham
Secluded Cabin on Golden Pond
Jul 27 – Aug 3
$161 per night
4.85 out of 5 average rating, 117 reviews
Guest favorite
Home in Coventry
Cozy Cottage * Coventry Lake* 15 min to UConn *
Jun 12 – 19
$162 per night
4.94 out of 5 average rating, 156 reviews
Guest favorite
Apartment in Stonington
Waterfront Marina Living
Jul 16 – 23
$170 per night
4.95 out of 5 average rating, 131 reviews

Connecticut house rentals

Guest favorite
Home in Cheshire
Pool House
Jan 15 – 22
$126 per night
5.0 out of 5 average rating, 116 reviews
Guest favorite
Home in Stamford
STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
Jul 6 – 13
$93 per night
4.98 out of 5 average rating, 130 reviews
Guest favorite
Home in New Haven
Q River House - 2 bdrm, minutes from Yale/Downtown
Dec 19 – 26
$157 per night
4.99 out of 5 average rating, 176 reviews
Guest favorite
Home in Danbury
BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!
Feb 2 – 9
$126 per night
4.99 out of 5 average rating, 335 reviews
Guest favorite
Home in Bristol
Cozy Family Home - Kid & Pet Friendly
Jan 19 – 26
$119 per night
4.92 out of 5 average rating, 101 reviews
Guest favorite
Home in Stonington
Romantic Seaside Cottage in Mystic
May 12 – 19
$214 per night
4.95 out of 5 average rating, 165 reviews
Guest favorite
Home in Old Lyme
Modern Farmhouse with Hot Tub in Old Lyme, CT
Dec 9 – 16
$347 per night
4.96 out of 5 average rating, 119 reviews
Guest favorite
Home in Washington
Country Home on a Hill
Jun 12 – 19
$113 per night
4.85 out of 5 average rating, 168 reviews
Guest favorite
Home in East Haven
Beach Cottage by the Sea
Jan 28 – Feb 4
$136 per night
4.88 out of 5 average rating, 194 reviews
Guest favorite
Home in Milford
The Daydreamer -Walk to Walnut Beach, Pet Friendly
Oct 26 – Nov 2
$200 per night
4.99 out of 5 average rating, 220 reviews
Guest favorite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
Feb 16 – 23
$132 per night
4.96 out of 5 average rating, 101 reviews
Guest favorite
Home in Manchester
Paradise On The Hill Luxury Apartment.
Jul 23 – 30
$86 per night
4.94 out of 5 average rating, 172 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