Family-friendly holiday rentals in Wilton

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Top-rated family-friendly rentals in Wilton

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

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Superhost
The living area features a neutral color palette with a contemporary couch and a low coffee table. A bar-style dining area with high stools is visible, complemented by a 42-inch Roku TV mounted on the wall. Natural light enters through a window, enhancing the inviting ambiance.
Apartment in Norwalk
4.91 out of 5 average rating, 340 reviews

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.

Top Guest favourite
A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.
Guest suite in Wilton
4.91 out of 5 average rating, 159 reviews

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Guest favourite
A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.
Apartment in Redding
4.94 out of 5 average rating, 491 reviews

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.

Guest favourite
A charming cottage exterior is surrounded by lush greenery and autumn foliage. The two-story structure features a balcony adorned with potted plants. Large windows create a welcoming appearance, while the grassy area in front offers a peaceful outdoor setting.
Guesthouse in Wilton
4.96 out of 5 average rating, 135 reviews

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.

Guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 176 reviews

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

Top Guest favourite
The bedroom is illuminated by natural light from multiple windows. A spacious bed is positioned alongside a wooden dresser and a small bookshelf. Two blue chairs flank a side table, creating a cozy seating area. Light oak flooring enhances the room's bright ambiance.
Apartment in South Norwalk
4.99 out of 5 average rating, 101 reviews

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.

Top Guest favourite
A cozy efficiency studio features a queen size bed with a patterned headboard, layered with a navy blanket. A bedside lamp provides soft lighting. On one side, a red couch and a decorative rug enhance the living space, while a closet with sliding doors is present.
Guest suite in Norwalk
4.92 out of 5 average rating, 165 reviews

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.

Guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 98 reviews

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.

Superhost
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.8 out of 5 average rating, 232 reviews

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.

Guest favourite
A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.
Place to stay in Southport
4.96 out of 5 average rating, 327 reviews

Sunny Westport 2 BR Retreat above Historic Mill

Historic Cider Mill Retreat – A Unique Stay for Leisure & Business Travelers Experience the charm of history blended seamlessly with modern comfort in this eclectic, sun-filled apartment perched atop a beautifully restored 1850s cider mill. Thoughtfully designed and furnished by our team of artisans, this unique getaway offers panoramic views, breathtaking surroundings, and a rich historical ambiance that makes for a truly unforgettable stay.

Guest favourite
A cozy sleeping area features a full-size bed with a gel memory foam topper, complemented by a light blanket. Natural light enters through a nearby window, illuminating the room. A closet with sliding doors provides additional storage, and a simple dresser is positioned against the wall.
Guest suite in West Norwalk
4.74 out of 5 average rating, 487 reviews

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

Enjoy a restful stay or shorten your commute in this cozy studio with easy access to highways, shops, and restaurants. The studio has a private entrance and onsite parking. It also has fast internet, a laptop-friendly workspace, and a kitchenette. Perfect for business travelers or 1-2 people. Pets are welcome with a non-refundable fee. ***Please read the entire listing prior to booking including “other things to note”***

Top Guest favourite
A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.
Guesthouse in South Salem
4.94 out of 5 average rating, 309 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.

Popular amenities for Wilton family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Wilton

  • Total rentals

    30 properties

  • Nightly prices starting at

    $216 AUD before taxes and fees

  • Total number of reviews

    380 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace