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

Total holiday rentals
Explore 60 holiday rentals in Westport

Nightly prices starting at
Westport holiday rentals start at $119 NZD per night before taxes and fees

Verified guest reviews
Over 2,220 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
60 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 pet-friendly home rentals in Westport
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
PetsOutdoor spacesComfort

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.
PetsWalkabilityParking

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.
WalkabilityOutdoor spacesLocation

Downtown Fairfield 3 bedroom Colonial
Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.
WalkabilityOutdoor spacesBeach

Private Studio Apartment; Kitchen; Fully Furnished
This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)
Outdoor spacesWalkabilityNearby

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.
PetsWalkabilityBackyard

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.
Outdoor spacesPetsLayout

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.
Outdoor spacesPetsTV

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.
WalkabilityOutdoor spacesHot tub

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.
Outdoor spacesPetsCleanliness

2BR Flat above Historic Cider Mill
Escape to a sun-filled, 2-bedroom artisan retreat in a restored 1850s cider mill. Overlooking a peaceful marsh near Westport & Southport, this unique space comfortably fits 4. Enjoy historic charm, modern comforts, a fully-stocked kitchen, and free access to a professional co-working space. Perfect for families, couples, or work-from-anywhere stays. Free parking included.
Outdoor spacesWalkabilityView

Cozy, romantic cabin by the lake.
This romantic, rustic and cozy lakeside cabin is the perfect place to unwind, relax and explore nature. There are miles of woodland trails to explore, and it is only 55 minutes from NYC, 5 minutes from the Merritt Parkway and other major highways, 20 min UBER from Metro North Train Fairfield Station, or Bridgeport.
Outdoor spacesPetsAir conditioning
Popular amenities for Westport pet-friendly home rentals
Pet-friendly house rentals

Fully renovated/Walk to water & shops/fenced yard!
PetsWalkabilityCheck-in

5BR Beach House, Game Room + Huge Backyard
Outdoor spacesWalkabilityCleanliness

Bright Stylish Chic 4BR 4BA Home
PetsWalkabilityLong stay

Comfortable home away from home- near everything
Outdoor spacesPetsGetting around

Gem by the water+ firepit and all fenced backyard
Outdoor spacesPetsDecor

Cozy Studio in Bridgeport
Outdoor spacesPetsBackyard

Boho house near NYC
Outdoor spacesPetsHospitality

The ARLO - Walk to Brewery & Restaurants
Outdoor spacesWalkabilityKitchen
Pet-friendly home rentals with a pool

Stamford Grand Apartment + Cozy Den
Outdoor spacesWalkabilityGetting around

3‑Acre Weston Retreat w/ Pool & Basketball Court
PetsOutdoor spacesCondition

Midcentury Modern ZenHouse Sculptor Studio
WalkabilityOutdoor spacesTV

Cozy studio unit
Outdoor spacesPetsValue

Spacious Cottage Loft
Outdoor spacesPetsComfort

Port Jefferson Convenient, Cozy and Chic!
WalkabilityOutdoor spacesHeating

Peaceful Light-Filled Guesthouse salt pool/sauna
PetsWalkabilityCleanliness

The Perch: Saltwater Pool Woodland Cottage Retreat
Outdoor spacesPetsAir conditioning
Private, pet-friendly home rentals

Walk to Compo Beach Renovated Westport Home
WalkabilityOutdoor spacesNearby

Westport CT, Hide-away!
Outdoor spacesPetsAmenities

River Cottage in Weston, CT
Outdoor spacesPetsCleanliness

Stareway to Heaven
PetsOutdoor spacesCleanliness

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
WalkabilityPetsBathroom

Private cottage in horse country &1 hour from NYC!
Outdoor spacesWalkabilityTV

Lakefront Cottage near Hudson Valley
WalkabilityPetsLayout

Westport Luxury Escape | 10 Minutes to Beach
PetsOutdoor spacesFamily
When is the best time to visit Westport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $383 NZD | $417 NZD | $468 NZD | $727 NZD | $962 NZD | $867 NZD | $594 NZD | $850 NZD | $468 NZD | $739 NZD | $514 NZD | $717 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
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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





