
Family-friendly vacation rentals in Westport
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Westport
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private
Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk
The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Spacious Westport Apt surrounded by nature!
Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

Huckleberry Quarters, the Cozy Redding Retreat.
It’s time to book your FALL LEAF-PEEPING sojourn at the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

S. Norwalk Apt near the water!
Newly-built sunny studio apartment with separate eat-in kithchen and spacious bath, across the street from the water in the peaceful waterfront community of Shorefront Park in South Norwalk. 15 min. walk to South Norwalk shops, restaraunts and the train station (65 min train ride to NYC). Private kepypad entrance, washer/dryer, eat-in kitchen, free off-street parking, wifi, central AC. Please note the house next door may be under construction. Please inquire for current status.

Fall Sale! CozyCottage/Pet-friendly/Walk to Beach
Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Efficiency Garden Studio in South Norwalk, CT
Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest suite with private enter
Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Sunny Westport Studio Apt. Above Historic Mill
Historic Charm Meets Modern Comfort: A Unique Studio Retreat Perched atop a restored 19th-century Cider Mill, this sunlit studio blends timeless character with modern amenities. Enjoy stunning views of a picturesque stream, serene meadows, and diverse wildlife. Just moments from Southport Village, yet offering a peaceful escape, it's perfect for history lovers, business travelers, and design enthusiasts seeking a unique getaway.
Popular amenities for Westport family-friendly rentals
Family-friendly home rentals with a hot tub

Coastal Villa Suite pool•sauna•gym•theater•beach

Foxglove Farm

Little Blue Heron-Idyllic log cabin w/hot tub!

Oceanfront Retreat with Hot Tub

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

The Hideaway

Beach Haven - waterfront, near Yale, sunsets

*Large Pool* Garrison Ultra Modern 5B hottub sauna
Family- and pet-friendly home rentals

Charming Guest Cottage with Modern Amenities

Small Studio. Private Entrance and bathroom

HGTV reno! Fall Foliage, near New Haven, Firepit!

Downtown Fairfield 3 bedroom Colonial

Private and Serene home close to I-84 and shopping

Hudson River Peaceful Getaway, Explore from here

Chic Beach Bungalow - Amazing Sunsets!

Cozy Cottage by the pond
Family-friendly home rentals with a pool

Artist Retreat in Beautiful Country Setting

Garden Level Suite with Beautiful Pool

Entire Guest House at Fox Pond Farm.

Fireplace, Huge Eclectic space… 1.5 hr to NYC!

Spacious Cottage Loft

King 1BR Apt with Cozy Den and Luxury Amenities

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Port Jefferson Convenient, Cozy and Chic!
When is the best time to visit Westport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,895 | ﺩ.ﺇ1,458 | ﺩ.ﺇ1,913 | ﺩ.ﺇ2,038 | ﺩ.ﺇ2,226 | ﺩ.ﺇ2,387 | ﺩ.ﺇ2,248 | ﺩ.ﺇ2,387 | ﺩ.ﺇ2,387 | ﺩ.ﺇ2,292 | ﺩ.ﺇ2,376 | ﺩ.ﺇ2,530 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about vacation rentals that are family-friendly in Westport

Total vacation rentals
Explore 110 vacation rentals in Westport

Nightly prices starting at
Westport vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 1,550 verified reviews to help you choose

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
110 of Westport vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westport rentals

4.9 Average rating
Westport stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Connecticut
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- Yale University
- MetLife Stadium
- Central Park Zoo
- Jones Beach
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