
Family-friendly holiday rentals in Westport
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Westport

Total holiday rentals
Explore 110 holiday rentals in Westport

Nightly prices starting at
Westport holiday rentals start at $272 NZD per night before taxes and fees

Verified guest reviews
Over 1,760 verified reviews to help you choose

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
110 of Westport holiday 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!
Top-rated family-friendly rentals in Westport
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen
Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.
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The Cozy Little Cottage
Charming guest apartment 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, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.
KitchenFamilyHeating

S. Norwalk Studio 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. 20 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. 2 night minimum Please note the house next door may be under construction. Please inquire for current status.
Indoor spacesKitchenAir conditioning

Private Guest Suite | Entrance, Bath & Parking
Private guest suite with a private entrance, attached bathroom, dedicated workspace, fast internet, and private parking. Located on a quiet 1.5-acre property in Wilton, CT, walking distance of ASML and close to Norwalk Corporate Park, downtown Wilton, restaurants, coffee shops, stores, parks, and the Norwalk train station. Owners live in a separate part of the house. Guests have private access and space. Pets are welcome, outdoor space for dog walks. Cats live here but do not enter the suite.
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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.
Indoor spacesFamilyLong stay

Family Cottage with 4 King Beds and Fire Pit
Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.
KitchenIndoor spacesBarbecue

Sunny French Cottage
This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)
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1BR full cottage, 1 min walk to private beach
Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.
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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
FamilyKitchenCleanliness

Oceanfront Beach House w/ Private Hot Tub
Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.
KitchenFamilyHot tub

Historic Loft, Co-Work, River View
Unique studio loft in a beautifully restored 19th-century Cider Mill on the Westport/Southport border. Enjoy picturesque river views, historic charm, and modern comfort. This pet-friendly retreat comfortably accommodates up to three guests, featuring a full kitchen, dedicated workspace, and access to a co-working space. Ideal for couples or solo travelers seeking a blend of history, convenience, and a serene setting with private parking.
Indoor spacesFamilyComfort

Beautifully Restored Barn With New England Charm
Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.
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Popular amenities for Westport family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Colonial - Private Hot Tub & Entire House
KitchenIndoor spacesSleep quality

Magic Red Barn with Heated Salt Pool (opened now)
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Bedford Paradise Getaway | Hot Tub | Town Center
Indoor spacesKitchenParking

3 Bedroom Beach House with Hot Tub!
FamilyKitchenCleanliness

Coastal Villa Suite pool•sauna•gym•theater•beach
Indoor spacesFamilyOutdoor spaces

Little Lake Cabin— Lake Access, Hot Tub & Kayaks
KitchenIndoor spacesParking

The Hilltop Harborview
FamilyKitchenHospitality

Luxury modern farmhouse with heated pool & hot tub
KitchenIndoor spacesPool
Family- and pet-friendly home rentals

Cozy, romantic cabin by the lake.
KitchenIndoor spacesAccess

Downtown Fairfield 3 bedroom Colonial
FamilyIndoor spacesSleep quality

The ARLO - Walk to Brewery & Restaurants
FamilyIndoor spacesOutdoor spaces

Private cottage in horse country &1 hour from NYC!
Indoor spacesKitchenShared spaces

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
KitchenIndoor spacesCondition

☆Charming Studio - Private/Self Check-In/Parking☆
Indoor spacesFamilyCondition

Cozy Studio in Bridgeport
Indoor spacesKitchenDecor

1956 House of the Year Award. Easy commute to NYC.
KitchenIndoor spacesCondition
Family-friendly home rentals with a pool

Private Guest Studio
Indoor spacesFamilyWalkability

Escape to a Restored New England Antique Milk Barn
KitchenIndoor spacesHeating

Spacious Cottage Loft
KitchenIndoor spacesGetting around

The Pond Mill Retreat w/ 2 Bdrms & Pool
KitchenFamilyOutdoor spaces

Huge eclectic space w/ private pool. 1.5hr to city
Indoor spacesFamilyPool

Midcentury Modern ZenHouse Sculptor Studio
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Port Jefferson Convenient, Cozy and Chic!
FamilyIndoor spacesAir conditioning

Garden Level Suite with Beautiful Pool
Indoor spacesFamilyPool
When is the best time to visit Westport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $885 NZD | $1,023 NZD | $811 NZD | $853 NZD | $1,115 NZD | $1,277 NZD | $1,129 NZD | $1,086 NZD | $1,076 NZD | $996 NZD | $1,022 NZD | $976 NZD |
| 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 |
Destinations to explore
- New York City Holiday rentals
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- Times Square
- Central Park Zoo
- Yale University
- Jones Beach
- Yankee Stadium
- Columbia University
- New York City Center
- American Dream
- MetLife Stadium
- Rockefeller Center
- United Nations Headquarters
- Bear Mountain State Park
- Empire State Building
- Barclays Center
- Bryant Park
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Brooklyn Bridge
- Radio City Music Hall
- Fairfield Beach
- Astoria Park
- Thunder Ridge Ski Area
- Bronx Zoo





