Skip to content

Westport summer vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Westport

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

Private room in Weston
Light Filled Loft on the River w/ Private Entrance
Open the doors to your private loft and enjoy the sounds of the babbling Saugatuck River in this one bed, one bath studio loft located in Weston, CT. This serene space is perfect for solo travelers, couples or small groups looking for a peaceful getaway. Just minutes from downtown Westport and an hour 15 to New York City, this unique space is close to it all, but secluded and wooded enough that you may be lucky enough to catch sight of some of our regulars - grey herons, river otters and more.
$105 per night
SUPERHOST
Vacation home in Westport
Your perfect Westport getaway is here!
Great location! Book your stay at the Benjamin on Franklin…walking distance to Westport train & all of the fun Saugatuck bars, restaurants & shops. During the summer, kayaking is only steps away. "Benji" is the newest sister property to popular "Minty" (Araminta on Thames) in Newport, RI. Updated, spacious and comfortable. 2 bedrooms, living room, eat in kitchen & both patio & porch. Book now to get our grand opening rates! Sorry but no pets or smoking. No exception. Pls don’t ask.
$168 per night
Place to stay in Southport
Sunny Westport Studio Apt. Above Historic Mill
No ugly duckling. Fall asleep to the sounds of a centurys-old waterfall in this sunny studio apartment, atop a renovated historic Mill. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway may be moments from Southport Village, but feels like many miles from everything. Original hardwood floors and updated amenities make for a charming place to rest your bones, if only for the evening.
$75 per night
SUPERHOST

Stay near Westport's top sights

Photo of Sherwood Island State Park
Sherwood Island State Park43 locals recommend
Photo of Whole Foods Market
Whole Foods Market22 locals recommend
Photo of Trader Joe's
Trader Joe's62 locals recommend
Photo of bartaco
bartaco71 locals recommend
Photo of Shake Shack
Shake Shack6 locals recommend
Photo of Black Duck Cafe
Black Duck Cafe13 locals recommend

Westport vacation rentals

Guesthouse in Wilton
The Cozy Little Cottage
$139 per night
SUPERHOST
Rental unit in Norwalk
studio with king size bed and private parking
$99 per night
SUPERHOST
Guest suite in Fairfield
Adorable private apt w/ W/D in lovely neighborhood
$107 per night
SUPERHOST
Private room in Westport
The Tavern Room
$88 per night
Guesthouse in Southport
Beach rental on Westport Gold Coast
$190 per night
SUPERHOST
Private room in Westport
Charming ,warm and inviting home
$100 per night
SUPERHOST
Guest suite in Norwalk
Efficiency Garden Studio in South Norwalk, CT
$75 per night
SUPERHOST
Private room in South Norwalk
Going solo? The World is Your Oyster: Norwalk
$59 per night
SUPERHOST
Guest suite in Norwalk
☆Charming Studio - Private/Self Check-In/Parking☆
$89 per night
Private room in Norwalk
Clean, Quiet and Comfy Bedroom! Fast WiFi.
$45 per night
SUPERHOST
Guest suite in Fairfield
Beautiful Private Entrance ensuite in Fairfield
$40 per night
Private room in Westport
Walk to town, Westport CT, Private Room
$130 per night
SUPERHOST

Westport beach vacation rentals

Cottage in Fairfield
Charming Fairfield Cottage By The Sea
$128 per night
SUPERHOST
Private room in Stamford
Great location , close to everywhere
$45 per night
SUPERHOST
Private room in Rowayton
Norwalk Home with Rowayton Amenities
$63 per night
SUPERHOST
Private room in Stamford
The Gold Room near downtown, trains, fast wifi
$47 per night
SUPERHOST
Private room in South Norwalk
Bright, cozy room with a beautiful view
$49 per night
SUPERHOST
Rental unit in Milford
Water front studio apartment with fireplace.
$129 per night
SUPERHOST
Cottage in Black Rock
King Bed Cottage w/ Relaxation Suite & Spa Shower
$129 per night
SUPERHOST
Guesthouse in Harbor Point
Private entrance, private bathroom, quiet zone.
$67 per night
Condo in South Norwalk
Studio in the heart of Downtown Norwalk
$94 per night
SUPERHOST
Rental unit in Stamford
Cozy guest apartment
$68 per night
SUPERHOST
Rental unit in Stamford
Spacious 1 bedroom Apartment Near Beach
$98 per night
SUPERHOST
Rental unit in Milford
One-bedroom Oasis by the Sound
$95 per night
SUPERHOST

Stays in Greens Farms

Loft in Black Rock
Cozy Loft in beautiful St. Mary's by the Sea
$97 per night
SUPERHOST
Guest suite in Fairfield
Separate Studio Apartment
$113 per night
SUPERHOST
Home in Fairfield
Downtown Fairfield
$144 per night
Private room in Bridgeport
Freshly Remodeled Room Near Historic Seaside Park
$49 per night

Stays in Saugatuck

Rental unit in South Norwalk
Water View SONO 2 Bedroom Walk to Metro & Dining
$126 per night
SUPERHOST
Private room in Stamford
STAMFORD - WELCOME TO NEW ENGLAND ! (Downstairs 1)
$55 per night
Private room in Stamford
Stamford Bohemian Room: 3 min to Downtown & Train
$58 per night
SUPERHOST
Private room in Norwalk
Quiet Room w. Queen Bed in Sea Captain House (#4)
$85 per night
SUPERHOST

Stays in Greenfield Hill

Private room in 特拉伯尔
Beautiful private bedroom
$39 per night
Private room in Bridgeport
affordable convenient room 0
$45 per night
Private room in Bridgeport
♥️Peaceful room ♥️
$40 per night
SUPERHOST
Private room in Bridgeport
Freshly Remodelled Room By Historic Seaside Park
$48 per night
  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Westport