Family-friendly holiday rentals in Winooski

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winooski

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

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Guest favourite
A warm seating area is presented with two patterned chairs and a matching sofa, arranged around a small table. A textured rug covers the wooden floor, complemented by a brick accent wall featuring decorative plants and framed artwork. Natural light streams through a nearby window.
Guest suite in Essex
4.83 out of 5 average rating, 157 reviews

Spacious Retro Apartment: Ground Level

Cozy basement apartment with separate entrance and natural light. Quiet neighborhood, close to bus route, and walkable distance to bars, restaurants, and center of Essex Junction. We welcome people from all walks of life, and all backgrounds into our warm, vintage chic apartment. Private space in our bustling house, you WILL HEAR us upstairs, please note!! Full bath with small shower, kitchenette with full fridge—no stove. Microwave, hot plate, toaster, Keurig coffee maker and washer and dryer.

Guest favourite
A bright living area is furnished with a spacious sectional sofa adorned with colorful cushions. Artistic wall decorations add visual interest, while a leafy plant and bookshelves bring a touch of greenery. A cozy reading nook featuring a small chair is also visible, along with a dining area.
Home in Winooski
4.95 out of 5 average rating, 553 reviews

Very clean and charming 2 BR, close to everything!

Enjoy this newly updated apartment in Winooski, VT (Vermont's Brooklyn). This charming house is one of the original carriage homes in Winooski. Newly converted to a duplex, enjoy this private apartment within walking distance to downtown Winooski's restaurants and bars. Less than 1 mile from the local colleges in Burlington and Colchester, including University of Vermont, St. Michaels College and Champlain College. You have your own private entrance with free parking for 2 cars in the driveway.

Guest favourite
The exterior of a charming red building is showcased, featuring a well-maintained yard. Two black outdoor chairs are positioned on the grass, inviting relaxation. Above, a wooden deck adorned with potted plants offers additional outdoor space, with a glimpse of nearby buildings visible.
Flat in Old North End
4.96 out of 5 average rating, 195 reviews

Purple Door Annex

Purple Door Annex features a lovingly renovated four-season building located in Burlington's historic Old North End District. A ten minute walk to Church Street and walkable to all of Burlington's City attractions. Purple Door Annex is an ideal space for guests seeking a fun getaway in the heart of the city that is private and well-appointed. Your hosts have five years of experience as superhosts in another bedroom on the premises and are excited to welcome you to this newly renovated space.

Guest favourite
The living area features a cozy dark couch facing a television and electric fireplace. A coffee table with a wood-patterned surface sits on a light area rug. A small kitchenette with granite countertops is equipped with a sink, and natural light enters through a nearby window.
Flat in New North End
4.84 out of 5 average rating, 282 reviews

Bright & adorable 1 bedroom studio with parking

Welcome to our delightful space located off the ave in Burlington's New North End! You've found a gem in a quiet section of the beautiful city of Burlington. We strive to offer travelers a place to rest that promises safety and comfort. This one bedroom apartment is a convenient 7 minute drive to downtown, 1 minute drive to the beach, and only a few blocks from the bike path/lake! We are located directly on the bus line, so even travelers without a vehicle can access all Vermont has to offer.

Top guest favourite
The exterior of the building is shown, featuring a screened porch with a slanted roof and a staircase leading to the front door. Two large windows provide natural light, and greenery surrounds the entrance, enhancing the overall inviting appearance.
Flat in Old North End
4.96 out of 5 average rating, 100 reviews

Jean’s Place

We welcome you to this one bedroom apartment in the heart of Burlington, Vermont. The unit is located in a professional neighborhood in the heart of the old north end district. This unit has separate upstairs accessibility. Plenty of bakeshops, breweries, cafes, restaurants located in the neighborhood . We are also just minutes away from the beautiful Lake Champlain waterfront with walking/bike friendly roads and paths, and more! No solicitation of any kind for this listing to this Airbnb.

Top guest favourite
A modern rustic cottage is illuminated by string lights in the evening sky, which displays warm hues of pink and orange. The exterior features wooden siding and large windows, while a cozy seating area with Adirondack chairs is visible in the shared yard.
Guest house in Winooski
4.98 out of 5 average rating, 362 reviews

Modern Rustic Backyard Cottage

This newly built modern rustic mother-in-law private cottage offers a convenient place to stay while exploring the Burlington/Winooski area. The cottage is nestled in my backyard on a quiet street in vibrant Winooski. The home is a 10 minute drive to downtown Burlington & the airport, and a short walk to the river, several cafes, restaurants, pubs, nature areas, and a brewery. Winooski is referred to as “the Brooklyn of Burlington” because of the foodie scene and rich cultural diversity.

Guest favourite
Bright interiors are enhanced by skylights, allowing natural light to fill the space. A comfortable gray sofa is positioned beside a cheerful yellow chair, with a round ottoman nearby. Colorful curtains frame the window, while a white dining table offers seating for meals.
Cottage in New North End
4.96 out of 5 average rating, 114 reviews

Brand New Cottage Near Burlington Park & Beaches -

This home situated across from Ethan Allen Park is just a short walk, bike ride, or drive to the North Ave beaches. Designed in keeping with the 1930's bungalow aesthetic of the main house, the cottage sleeps up to 4 with a queen-sized bed in the bedroom and queen-sized pullout sofa in the living room. Skylights brighten the lofty interiors. The cottage is well insulated and features centrally ducted heat and A/C, providing excellent climate control to suit your comfort preferences.

Superhost
A modern kitchen is equipped with stainless steel appliances, including a refrigerator, dishwasher, and microwave. Light cabinetry contrasts with decorative backsplash tiles. A wood countertop provides workspace beside a coffee maker, ensuring a functional and welcoming cooking area.
Flat in Winooski
4.83 out of 5 average rating, 116 reviews

Mini Mod Apartment, Private- Parking

1st floor private little apartment (280sft!). Totally updated and modern, little spot with a private entry and private feel as it is around back. Has a washer dryer, petitie kitchen, bathroom, large bedroom/ room. And small porch. Pet friendly with a private yard. Comes with one designated parking spot. Be right downtown in Winooski and walk to downtown. Only a quick 5 min drive to UVM or Church Street! 15%weekly stay discount 30%monthly!!

Superhost
A simple wooden dining table is situated in a bright room, surrounded by four wooden chairs. Natural light filters through sheer white curtains, creating a light and airy environment. A potted plant sits on the table, adding a touch of greenery.
Guest suite in Old North End
4.81 out of 5 average rating, 483 reviews

Old North End Guest Suite

Our property is located on a quiet street in Burlington's Old North End. Recently renovated the guest suite sits above our home and is equipped with a private entrance. Windows face west providing a good deal of natural light. The partial kitchen is located in a small room off of the bedroom. The kitchen is equipped with a sink, small refrigerator and freezer, toaster oven, microwave, and an electric kettle. Private bathroom. Wifi is provided.

Top guest favourite
A bright living area features a large television displaying an underwater scene with a turtle. A circular glass coffee table is centered between a sleek black sofa and a plush seating area. Light pours in through expansive windows, highlighting a colorful area rug and a potted plant.
Flat in Winooski
4.92 out of 5 average rating, 328 reviews

Luxe Zen-Den Ski Haus Brewers walk-shop-dine UVM

While waiting for check-in: pvt dog run and restaurants on site! Excellent drinks and dining on the first floor with many more restaurants a short walk away! 2.5 m to Church St, 1+ m to UVM, the Riverwalk, and Breweries. Whether you're here to hit the slopes, explore the beaches, or sample local brews at Four Quarters brewery, enjoy our fully accessible location for your lake Champlain adventures! Book now for the best of Vermont.

Top guest favourite
The Tiny Home is nestled among snow-covered trees, featuring a warm wooden exterior and a sloped roof. Soft lighting emanates from multiple windows, illuminating a welcoming entryway with a red door. Steps lead up to the porch, inviting guests inside.
Tiny home in Shelburne
4.9 out of 5 average rating, 397 reviews

Cozy Tiny House Minutes to Downtown Shelburne

220 sq. foot charming Tiny Home under tall pines with a covered porch. Great space for solo travelers and couples that like to be cozy! The rustic interior has a full kitchen, copper shower, and compost toilet. The loft bedroom is serene with 5 windows and blackout curtains (in case you want to sleep in!). Just 12 minutes to Burlington. 4 minutes to downtown Shelburne and Shelburne Museum.

Top guest favourite
A modern studio apartment features a spacious bed with a cozy purple throw, complemented by a small dining table and white accent chairs. Natural light floods in through two windows dressed with dark curtains, while a well-equipped kitchenette and a bathroom area are accessible in the background.
Guest suite in Winooski
4.96 out of 5 average rating, 591 reviews

Modern Winooski Studio-Walkable to Winooski Circle

Modern, renovated studio apartment, slightly larger than most hotel rooms, within walking distance of Winooski’s bars and restaurants. And we're just a few miles (bikeable or driving) to downtown Burlington, UVM, Champlain College, and St. Michael’s College. Easy highway access means quick drives to all that Vermont has to offer. City of Winooski Short-Term Rental License #24103

Popular amenities for Winooski family-friendly rentals

When is the best time to visit Winooski?

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Avg. price$178 SGD$197 SGD$188 SGD$193 SGD$223 SGD$204 SGD$223 SGD$231 SGD$218 SGD$244 SGD$184 SGD$182 SGD
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Quick stats about holiday rentals that are family-friendly in Winooski

  • Total holiday rentals

    Explore 60 holiday rentals in Winooski

  • Nightly prices starting at

    Winooski holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,350 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Winooski holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winooski rentals

  • 4.8 Average rating

    Winooski stays are highly rated by guests – averaging 4.8 out of 5!