Family-friendly vacation rentals in Winooski

4.95 out of 5 average rating, 578 reviews

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

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.

FamilyIndoor spacesSleep quality

4.98 out of 5 average rating, 394 reviews

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.

Guesthouse in Winooski

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.

Indoor spacesKitchenSleep quality

4.83 out of 5 average rating, 129 reviews

A bright entryway is highlighted by a bold blue front door featuring a grid pattern of windows. To the right, a yellow tufted bench offers seating, while a patterned rug adds contrast. The space is complemented by light-colored walls and wood flooring, creating an open atmosphere.

Home in Winooski

Lovely Lil’ House- fenced yard!/Hot Tub

Small private 2 bedroom house with fenced in yard- Located right downtown! Walk to coffee shops, restaurants, brewery’s, etc..!! All details and amenities in place at this small private very sunny home with nice fenced in yard!! -65” flatscreen, wifi ready tv -Dedicated work space -Private fenced in back yard -BBQ -Full kitchen- -Full coffee station -Modern new furniture -Pet Friendly -Plenty of Parking -Walk to restaurants, Coffee shops, brewery, etc- Central location -Washer/Dryer

Indoor spacesKitchenLaundry

4.98 out of 5 average rating, 109 reviews

Burlington area “neighborhood” location

You will enjoy easy access to everything in the greater Burlington area -Airport BTV -University of Vermont, Champlain College, St Michael's College -UVMMC Hospital and Medical Center -Champlain Valley Expo -Respite Center The space is very well-appointed and comfortable. One bedroom with queen bed Second bedroom is two daybeds in the living area. Kitchen and washer/dryer Private entrance on right side of the home. See photo showing private entrance down short stairway under portico

KitchenIndoor spacesCondition

5 out of 5 average rating, 388 reviews

An aerial view captures the shared outdoor space, featuring a grassy area surrounded by vibrant flowers and greenery. A wooden deck leads to the entry of the tiny house, accompanied by several seating options, including chairs and a table shaded by an umbrella.

Tiny home in Winooski

Tiny House by Winooski Falls, Vermont River House

River House is across from the Winooski Falls and is part of Burlington's historic mill neighborhood. It's a 10 minute walk to the Winooski Circle which is full of restaurants and activity. Downtown Burlington and Lake Champlain are a 10 min (2 mile) drive away. This unique, arty tiny house features hardwood floors, a small kitchen and bathroom, and a shared outdoor space. There is a queen bed upstairs in the loft and a full sized couch downstairs which can be made up for sleeping.

FamilyIndoor spacesNearby

Guest suite in Colchester

A cozy bedroom features a spacious bed with neutral bedding and decorative pillows. Two bedside lamps are positioned on each side of the bed. Natural light enters through a window adorned with light curtains. A minimalist clothing rack is situated against one wall.

4.88 out of 5 average rating, 200 reviews

Cozy 1 Bedroom Apartment Getaway

Kick back and relax in this calm, cozy space! Enjoy an updated bathroom and bedroom, relax on the couch or eat a nice meal at the breakfast bar! This apartment is close to the lake, bike path, great bars and dining, and just a short drive to the mountains. There’s a small park across the street with a tennis court, basketball court and playground! Bayside Park Beach Access - 8 mins Church Street Marketplace, Burlington - 18 mins Stowe Mountain - 60 mins Smugglers Notch - 42 mins

Indoor spacesFamilyHiking

4.8 out of 5 average rating, 101 reviews

Home in Burlington

Second story stay

Welcome to our Cozy Second-Floor Retreat in downtown Burlington, VT! Located in the historic Old North End, this private apartment is upstairs in our 200 year old house! The space is quirky but also offers comfort and convenience. It’s a short walk to great food, drink, and entertainment, and just minutes from the Church Street Marketplace. The space is warm and inviting, thoughtfully designed with books, games and smart TV to accommodate guests and pets for a comfortable stay.

KitchenIndoor spacesParking

4.94 out of 5 average rating, 187 reviews

A wooden bridge leads to the entrance of the treehouse, surrounded by trees displaying autumn colors. The structure features large windows and a unique architectural design, blending nature with handcrafted elements.

Treehouse in Waterbury

The Roost - Recharge & Relax

Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.

FamilyIndoor spacesHot tub

4.99 out of 5 average rating, 208 reviews

An open-concept kitchen and living area is highlighted by a spiral staircase leading to a loft. A modern kitchen features stainless steel appliances and a central island with two stools. Natural light flows through a front door, creating a bright and inviting space.

Tiny home in Burlington

theLOFT | Burlington, VT

Thoughtfully designed with modern touches, local art, and cozy vibes and just a 15-minute stroll from the heart of downtown! Perfect for solo travelers or couples looking for a clean, comfortable, and convenient stay to kick back or explore; close to eateries, breweries, music, and everything the city has to offer. Inside, smart space utilization and brilliant lighting create a chic, inviting atmosphere. We can’t wait to see you soon!

Indoor spacesKitchenLaundry

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.

4.92 out of 5 average rating, 369 reviews

Luxe Zen-Den Golf Club Brewers walk-shop-dine UVMC

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.

KitchenIndoor spacesParks

A cozy space is showcased, featuring a kitchenette with essential appliances, a dining area with a small table and chairs, and a spacious bed set against the wall. Natural light filters through a window, enhancing the overall comfort of the area.

4.94 out of 5 average rating, 290 reviews

Barn Studio with sauna- garage door, heated or AC

Cozy downstairs of a converted barn with efficient rinai heater, AC, wood-fired sauna, both inside and outdoor showers, new Casper queen-sized bed and kitchenette w/keurig, hot water kettle, microwave, toaster oven, mini-fridge, and electric coils to cook on. Fire pit and seating outdoors and sauna indoors we can start for you. Quiet long-term tenants live above. STR License: 24104

Indoor spacesFamilyWalkability

Superhost

A cozy sleeping area features a spacious bed covered with a patterned blue quilt. Natural light floods in through multiple windows, highlighting a framed artwork above the bed. An armchair is positioned beside a side table, complementing the modern decor and inviting atmosphere.

4.85 out of 5 average rating, 539 reviews

Cute Apartment in the Heart of Winooski

Enjoy a bright and cozy studio apartment in the heart of downtown Winooski. A one minute walk to restaurants, cafés, breweries, and the scenic riverwalk. This comfortable home features a fully equipped kitchen, Smart TV, fast WiFi, and free parking. Just minutes from Burlington and the waterfront, it’s the perfect base for work trips, weekend getaways, and exploring Vermont.

FamilyIndoor spacesQuiet

Popular amenities for Winooski family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 160 reviews

The front of the cabin is framed by lush greenery and features a welcoming red door. Around a cozy patio area, four classic Adirondack chairs are arranged, complemented by blooming flower pots offering vibrant colors.

Cabin in Keeseville

Adirondack Cabin Retreat – Hot Tub + Lake

Indoor spacesKitchenLong stay

4.99 out of 5 average rating, 200 reviews

A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.

Cottage in Fletcher

Metcalf Pond Camp Convenient to Smugglers Notch

Indoor spacesFamilyCleanliness

A bright living room is highlighted by natural light from large windows. Light grey furniture complements the wooden flooring. A cozy area rug sits beneath a small coffee table. A wall-mounted TV and decorative shelves add to the welcoming atmosphere.

5 out of 5 average rating, 223 reviews

Charming Private Apt in South End w/ Hot Tub

KitchenIndoor spacesParking

4.92 out of 5 average rating, 110 reviews

A spacious living area is designed with light-colored furnishings, including a large sectional sofa and a matching armchair. Natural light floods in through multiple windows. A wall-mounted television is positioned above a low cabinet, creating a cozy atmosphere for relaxation and entertainment.

Home in South Burlington

So. Burl. quiet setting 10 mins fr. everything

KitchenFamilyGetting around

4.96 out of 5 average rating, 128 reviews

A charming two-story house is viewed at dusk, displaying warm lights glowing through its windows. An American flag waves gently outside, and a spacious deck can be seen to the right, surrounded by neatly kept grass and trees in the background.

Home in Williston

Convenient Cape | Explore Burlington & Stowe

Indoor spacesKitchenOutdoor spaces

4.99 out of 5 average rating, 161 reviews

The charming exterior of a classic cabin is surrounded by lush greenery, with a well-maintained front yard featuring flowering shrubs. A covered porch, adorned with hanging plants, invites relaxation, while the cabin’s traditional wood siding and gabled roof contribute to its rustic appeal.

Cabin in Stowe

Adorable Stowe Cabin w/ Hot Tub, River, Wood Stove

Indoor spacesFamilyCheckout

4.98 out of 5 average rating, 213 reviews

An aerial view captures a charming barn-style home surrounded by lush greenery, with expansive views of a serene lake in the background. The property features meticulously maintained lawns and a landscape rich in trees, set against a backdrop of rolling hills and distant mountains.

Barn in Hinesburg

Cozy Cabin -Top of Hill with Views

FamilyKitchenLong stay

Guest suite in Burlington

An outdoor courtyard features a salt-water hot tub and natural wooden seating. Lush greenery envelops the space, creating an intimate feel. A rustic barrel-shaped structure adds a unique element to the design. The ground is covered in smooth gravel, enhancing the serene atmosphere.

4.98 out of 5 average rating, 273 reviews

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

Indoor spacesKitchenCondition

Family- and pet-friendly home rentals

Two inviting chairs are positioned near a bay window, offering a view of a colorful sunset. The soft hues of the sky contrast with the dark silhouettes of trees outside, creating a serene atmosphere. A small side table is located between the chairs.

5 out of 5 average rating, 199 reviews

Hill Section Carriage House

FamilyIndoor spacesParks

4.97 out of 5 average rating, 468 reviews

A rustic cabin is viewed from the side, featuring a wooden deck with steps leading up to the entrance. Outdoor seating is positioned under a pergola. Flower pots add a splash of color to the cabin's exterior, surrounded by greenery.

Cabin in Keeseville

The Minouche - Cabin Life at its Best

KitchenFamilySleep quality

A living area is presented featuring a spacious futon adorned with colorful cushions, positioned against a backdrop of exposed brick. A large artwork dominates one wall, complemented by wooden beams overhead. Natural light floods through the windows, enhancing the relaxed atmosphere.

4.96 out of 5 average rating, 226 reviews

Downtown Burlington, Renovated, 1 bedroom+

FamilyKitchenHiking

4.98 out of 5 average rating, 119 reviews

A landscaped pathway with natural stone steps leads to a rustic log cabin, framed by lush greenery. The cabin features a warm wooden exterior, complemented by a surrounding garden with various plants. A decorative bell is positioned near the pathway.

Cabin in South Hero

The Cabin @ The Birches

Indoor spacesKitchenSleep quality

An open living area features high ceilings with ample natural light illuminating the space. A dining table is surrounded by black chairs, while a cozy seating area includes a vibrant sofa. A patterned rug lies beneath, enhancing the warmth of the environment.

4.98 out of 5 average rating, 297 reviews

Hyde Away | Spacious funky loft w/ parking & tub

FamilyIndoor spacesAccess

4.94 out of 5 average rating, 234 reviews

A small kitchen area is highlighted by large windows, offering views of the surrounding forest. A compact dining nook with cushions is situated next to a silver kitchen counter featuring a modern sink and a three-burner gas stove. Plants are positioned on the window ledges.

Tiny home in Richmond

Tiny on the Hill - Sauna + Burlington + Stowe

Indoor spacesKitchenLong stay

A charming exterior view showcases a cozy home with wooden shingles and a warm color palette. A private deck is adorned with seating options and is surrounded by greenery, including a flowering tree. Large glass doors provide access to the interior, while a fenced yard ensures privacy.

4.96 out of 5 average rating, 589 reviews

Cozy Burlington Getaway w/ Private Deck & Yard

KitchenFamilyAmenities

5 out of 5 average rating, 204 reviews

A spacious cabin is set in a lush green landscape, surrounded by tall trees. Large windows dominate the front, allowing natural light to fill the interior. The sloped grassy yard leads to a relaxing outdoor space, perfect for enjoying the serene woodland views.

Cabin in Enosburg

The Rustic Retreat at Twin Ponds

FamilyKitchenOutdoor spaces

Family-friendly home rentals with a pool

Guesthouse in Montgomery Center

A guest cabin nestled in the woods is visible, featuring a spacious green yard and a flowing brook nearby. A hammock hangs between trees, while red outdoor chairs are arranged around a stone fire pit. The cabin's elevated deck overlooks the serene landscape.

4.97 out of 5 average rating, 406 reviews

Cabin in the Woods VT - Discount Jay Peak Lift Tix

FamilyIndoor spacesComfort

4.98 out of 5 average rating, 167 reviews

A dining area is presented with a long wooden table, surrounded by several gray chairs. Two built-in benches with patterned cushions and pillows are positioned along the wall. A round mirror is mounted above the table, reflecting the space's natural light.

Townhouse in Stowe

Stowe, Newly Renovated Topnotch Resort Townhouse

FamilyKitchenLayout

4.94 out of 5 average rating, 481 reviews

A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

FamilyKitchenCleanliness

4.98 out of 5 average rating, 133 reviews

A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.

Apartment in Monkton

Spacious Private Apartment w/ Green Mountain Views

KitchenIndoor spacesBathroom

4.89 out of 5 average rating, 249 reviews

A spacious living room features a large brown leather sofa with decorative pillows, accompanied by two armchairs. A wooden coffee table sits on an oriental-style rug, and a couple of framed artworks adorn the walls. Floor-to-ceiling windows provide an airy atmosphere.

Townhouse in Stowe

Gorgeous panoramic views - 4 miles to the mountain

FamilyIndoor spacesPool

4.9 out of 5 average rating, 132 reviews

A warm, inviting living area features a comfortable sofa adorned with patterned throw pillows. Natural wood paneling enhances the space, while a large mirror reflects light. A staircase leads to an upper loft, and a dining table is visible in the background.

Condo in Cambridge

The Cozy Condo at Smuggs Resort!

KitchenIndoor spacesLocation

Guest suite in Starksboro

A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.

4.95 out of 5 average rating, 150 reviews

Private Suite in the Green Mountains

Indoor spacesFamilyLocation