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.
Apartment in Milford
4.97 out of 5 average rating, 505 reviewsWater 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 27 – Sep 3
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.
May 3 – 10
Guest suite in Wallingford
5.0 out of 5 average rating, 495 reviewsWintergreen 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 18 – 25
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Connecticut vacation rentals
Connecticut waterfront vacation rentals
Home in Milford
4.98 out of 5 average rating, 147 reviewsDesigner Beach Retreat on Exclusive Cedar Beach
Nov 21 – 28
Bungalow in Old Lyme
4.93 out of 5 average rating, 248 reviewsPet Friendly Bungalow!!!
Sep 11 – 18
Tiny home in Norwich
4.99 out of 5 average rating, 756 reviewsWater Forest Retreat -Octagon
Jan 29 – Feb 5
Cottage in Watertown
4.81 out of 5 average rating, 129 reviewsLakefront Cottage with Private Dock in CT
Apr 6 – 13
Home in Preston
4.96 out of 5 average rating, 595 reviewsEntire House Magical Waterfront Getaway
Dec 29 – Jan 5
Home in Stamford
4.97 out of 5 average rating, 217 reviewsMidcentury Modern ZenHouse Sculptor Studio
Nov 15 – 22
Cabin in North Stonington
4.95 out of 5 average rating, 146 reviewsCome unplug in the woods 15 mins from Mystic
Jul 8 – 15
Home in Branford
4.91 out of 5 average rating, 361 reviewsAdorable Beach House on the Long Island Sound
May 5 – 10
Home in Preston
5.0 out of 5 average rating, 117 reviewsNew Lake Front Home w/ Game Room & Stunning Views
Sep 12 – 19
Cottage in Guilford
4.96 out of 5 average rating, 157 reviewsLuxury cottage by the sea with hot tub and pool
Feb 11 – 18
Apartment in New Haven
4.89 out of 5 average rating, 465 reviewsFair Haven Heights Entire 1 Bedroom Apartment
Sep 19 – 26
Home in Lyme
4.97 out of 5 average rating, 185 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
Sep 28 – Oct 5
Connecticut fishing vacation rentals
Guesthouse in Southbury
4.93 out of 5 average rating, 265 reviewsCharming Guest Cottage with Modern Amenities
May 19 – 26
Guest suite in Thompson
4.98 out of 5 average rating, 112 reviewsMeadowside: Perfect Location w/ Endless Recreation
Aug 19 – 26
Cabin in New Fairfield
4.98 out of 5 average rating, 252 reviewsThe Little Lake Cabin— hot tub, fire pit, & kayaks
Nov 21 – 28
Apartment in Deep River
4.82 out of 5 average rating, 170 reviewsLoft apartment, deck and great water view
Nov 8 – 15
Cottage in Killingly
4.94 out of 5 average rating, 419 reviewsLake front cottage
Dec 4 – 11
Cottage in Chester
4.98 out of 5 average rating, 226 reviewsUpdated cottage "Beriozka" on Cedar Lake
Aug 9 – 16
Cottage in Middlefield
4.93 out of 5 average rating, 228 reviewsLake Beseck cottage
Oct 1 – 8
Cottage in Ledyard
4.92 out of 5 average rating, 199 reviewsLakeside cottage with beautiful views up the lake!
Nov 28 – Dec 5
Apartment in East Lyme
4.97 out of 5 average rating, 162 reviewsBrand New Direct Lakefront - Panoramic Sunsets
May 15 – 22
Home in Vernon
4.99 out of 5 average rating, 113 reviewsLuxe Bolton Lake!
Oct 15 – 22
Home in Coventry
4.94 out of 5 average rating, 157 reviewsCozy Cottage * Coventry Lake* 15 min to UConn *
Jun 21 – 28
Cottage in Lebanon
4.86 out of 5 average rating, 134 reviewsGo Jump in the Lake!
Dec 28 – Jan 4
Connecticut house rentals
Home in Stamford
4.98 out of 5 average rating, 130 reviewsSTAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
Apr 13 – 20
Home in East Lyme
4.96 out of 5 average rating, 103 reviewsWalk to the beach at Black Point, Niantic, Ct
Mar 3 – 10
Home in Danbury
4.99 out of 5 average rating, 335 reviewsBEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!
Nov 16 – 23
Home in Bristol
4.92 out of 5 average rating, 102 reviewsCozy Family Home - Kid & Pet Friendly
Jan 23 – 30
Home in East Haven
4.88 out of 5 average rating, 195 reviewsBeach Cottage by the Sea
Mar 16 – 23
Home in Manchester
4.94 out of 5 average rating, 172 reviewsParadise On The Hill Luxury Apartment.
Dec 4 – 11
Home in Cornwall
4.92 out of 5 average rating, 223 reviewsSecluded modern forest cabin with private brook
Dec 14 – 21
Home in New Haven
4.99 out of 5 average rating, 179 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
Dec 11 – 18
Home in Stonington
4.95 out of 5 average rating, 166 reviewsRomantic Seaside Cottage in Mystic
Nov 12 – 19
Home in Milford
4.99 out of 5 average rating, 223 reviewsThe Daydreamer -Walk to Walnut Beach, Pet Friendly
Aug 17 – 24
Home in Old Lyme
4.96 out of 5 average rating, 122 reviewsModern Farmhouse with Hot Tub in Old Lyme, CT
Oct 28 – Nov 4
Home in Washington
4.85 out of 5 average rating, 168 reviewsCountry Home on a Hill
Mar 19 – 26
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.
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