Connecticut vacation rentals

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Popular amenities for Connecticut vacation rentals

Connecticut oceanfront vacation rentals

Guest favorite

Home in Milford

4.98 out of 5 average rating, 152 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Oct 11 – 18

G$65,960 GYD per night
Superhost

Home in East Haven

4.88 out of 5 average rating, 196 reviews

Beach Cottage by the Sea

Nov 16 – 23

G$32,435 GYD per night
Guest favorite

Cabin in Voluntown

4.95 out of 5 average rating, 670 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

Oct 8 – 15

G$33,730 GYD per night
Guest favorite

Guest suite in Groton

4.9 out of 5 average rating, 156 reviews

Shoreline Retreat Groton-Mystic Region

Jul 8 – 15

G$24,398 GYD per night
Superhost

Loft in Bridgeport

4.86 out of 5 average rating, 173 reviews

Cozy Loft in beautiful St. Mary's by the Sea

May 2 – 9

G$34,449 GYD per night
Guest favorite

Apartment in East Lyme

4.97 out of 5 average rating, 167 reviews

Brand New Direct Lakefront - Panoramic Sunsets

Jul 2 – 9

G$109,634 GYD per night
Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 reviews

Updated cottage "Beriozka" on Cedar Lake

Mar 5 – 12

G$44,410 GYD per night
Guest favorite

Guesthouse in Fairfield

4.96 out of 5 average rating, 172 reviews

Southport, CT across from BEACH

Mar 30 – Apr 6

G$54,608 GYD per night

Connecticut fishing vacation rentals

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 reviews

Charming Guest Cottage with Modern Amenities

Aug 20 – 27

G$32,365 GYD per night
Guest favorite

Bungalow in Old Lyme

4.93 out of 5 average rating, 252 reviews

Pet Friendly Bungalow!!!

Feb 6 – 13

G$39,318 GYD per night
Guest favorite

Apartment in Deep River

4.82 out of 5 average rating, 171 reviews

Loft apartment, deck and great water view

Jul 9 – 16

G$25,455 GYD per night
Guest favorite

Cabin in North Stonington

4.95 out of 5 average rating, 147 reviews

Come unplug in the woods 15 mins from Mystic

Jul 5 – 12

G$39,412 GYD per night
Guest favorite

Guest suite in Thompson

4.98 out of 5 average rating, 114 reviews

Meadowside: Perfect Location w/ Endless Recreation

Aug 23 – 30

G$31,097 GYD per night
Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 256 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Feb 18 – 25

G$64,099 GYD per night
Guest favorite

Home in Stamford

4.97 out of 5 average rating, 218 reviews

Midcentury Modern ZenHouse Sculptor Studio

May 30 – Jun 6

G$96,774 GYD per night
Guest favorite

Apartment in New Haven

4.89 out of 5 average rating, 466 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Sep 4 – 11

G$23,906 GYD per night

Connecticut house rentals

Guest favorite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Aug 30 – Sep 6

G$20,244 GYD per night
Guest favorite

Home in Wilton

4.93 out of 5 average rating, 160 reviews

Mid Century Modern Cottage

Oct 29 – Nov 5

G$31,147 GYD per night
Guest favorite

Home in Preston

4.96 out of 5 average rating, 598 reviews

Entire House Magical Waterfront Getaway

Dec 29 – Jan 5

G$38,412 GYD per night
Guest favorite

Home in Manchester

4.94 out of 5 average rating, 174 reviews

Paradise On The Hill Luxury Apartment.

Aug 19 – 26

G$20,591 GYD per night
Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 117 reviews

Pool House

Jan 6 – 13

G$30,176 GYD per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Mar 9 – 16

G$31,726 GYD per night
Guest favorite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Dec 4 – 11

G$33,723 GYD per night
Guest favorite

Home in New Haven

4.99 out of 5 average rating, 184 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

Sep 15 – 22

G$37,578 GYD 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