Pet-friendly holiday rentals in Weston

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Weston

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in Fairfield

4.96 out of 5 average rating, 290 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

1–8 Dec

$503 NZD per night

Guest favourite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

28 Sep – 5 Oct

$305 NZD per night

Guest favourite

Apartment in Westport

4.92 out of 5 average rating, 118 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. 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 up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

24 Feb – 3 Mar

$336 NZD per night

Guest favourite

Guesthouse in Norwalk

4.99 out of 5 average rating, 209 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

19–26 Mar

$244 NZD per night

Guest favourite

Guesthouse in Norwalk

5.0 out of 5 average rating, 115 reviews

Private one bedroom cottage on Conn. seashore

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 friendly town; you don't even need a car while here.

11–16 Jul

$675 NZD per night

Guest favourite

Cottage in Milford

4.96 out of 5 average rating, 236 reviews

Spring Sale! Cozy Cottage | Walk to Beach | Pet

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.

20–27 Nov

$364 NZD per night

Guest favourite

Guest suite in Fairfield

4.94 out of 5 average rating, 361 reviews

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 University; an easy train ride to NYC. Please let us know how many beds you need.

21–28 Mar

$262 NZD per night

Guest favourite

Home in Pound Ridge

5.0 out of 5 average rating, 126 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Enter a freshly updated and thoughtfully furnished peaceful home surrounded by 14 acres of ancient trees, stone walls, and open meadows, in the town of Pound Ridge, NY. This natural light-filled guesthouse features all the elements needed to relax and unwind. In the summer months, guests have access to a heated saltwater pool, bask in the sun under a majestic maple tree, and enjoy the outdoor fire pit while stargazing at night.

14–21 Dec

$1,248 NZD per night

Guest favourite

Guesthouse in Mahopac

4.96 out of 5 average rating, 113 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

23–30 Oct

$230 NZD per night

Guest favourite

Cabin in New Fairfield

4.98 out of 5 average rating, 258 reviews

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

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars. Find us on IG @thelittlecabins

3–10 Mar

$542 NZD per night

Guest favourite

Place to stay in Westport

4.95 out of 5 average rating, 281 reviews

Sunny Westport 2 BR Retreat above Historic Mill

This eclectic, sunny, spot, sits above a renovated historic cider mill from the 1850s. It has been designed and furnished by our own team of artisans. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway is the perfect "Get Away."

26 Feb – 5 Mar

$379 NZD per night

Guest favourite

Guesthouse in South Salem

4.93 out of 5 average rating, 220 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

29 Sep – 6 Oct

$358 NZD per night