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Kid-friendly vacation rentals in Winhall

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Winhall kid-friendly rentals

Kid-friendly house rentals

Guest favorite
A wooden bookshelf showcases a variety of colorful books arranged neatly. A ladder provides access to a cozy lofted sleeping area, while a blue cabinet and framed art complete the space. A clock hangs on the wall, adding a functional touch.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favorite
A single-story ranch home is surrounded by a lush green lawn, featuring a welcoming front deck with white railings. Dark shutters frame the windows, and colorful flowers add a touch of vibrancy to the landscape. A patio area is visible in the background.
Home in Manchester
4.85 out of 5 average rating, 227 reviews

Keys to Vermont

ElizabethRating, 5 stars1 month ago
Mary’s place was a great location for us to stay during our ski trip to Bromley. We were within a 10min drive to skiing and 5 minute drive to the restaurants in town. The beds were very comfortable and the bathrooms nice and clean. We randomly had cassette tapes with us and Mary had a tape player, the kids were soo excited to use it. She also had games and books for the kids. We had a great time! Thank you!
Superhost
The charming exterior of a farmhouse is surrounded by lush greenery, featuring a pale blue façade and a welcoming pink door. Dense foliage and colorful flowering plants enhance the inviting approach to the home, set against a peaceful landscape.
Home in Londonderry
4.94 out of 5 average rating, 174 reviews

Clean, Captivating VT Farmhouse near Stratton!

JamesRating, 5 stars2 months ago
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.
Top guest favorite
A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Superhost
A playful children's corner features a white teepee adorned with string lights. Nearby, a faux campfire setup with red and orange flames positioned on gray stones creates an engaging atmosphere. A light green wall and soft carpet enhance the inviting space.
Home in Bridgewater
4.86 out of 5 average rating, 125 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

BrianRating, 5 stars3 days ago
Chris isn't joking that he likes to keep the kitchen well stocked. It was great having everything that a typical kitchen would have at your convenience. The views were gorgeous and were really enjoyable when relaxing in the hot tub. Our three boys loved the kids room and that there were toys to play with. The location made our Vermont stay all that much more enjoyable, thank you for the great memories!
Superhost
A serene winter scene captures a two-story house blanketed in fresh snow. Flakes gently fall, creating a soft ambiance. The front yard features a large evergreen tree, while the warm glow of an interior light is visible through a window, hinting at a cozy atmosphere inside.
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars1 month ago
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars1 week ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Top guest favorite
An open dining area features a large wooden table surrounded by white chairs. Natural light fills the space from multiple windows, highlighting rustic wooden beams above. A cozy seating nook with plants and a decorative fireplace creates a welcoming ambiance.
Home in Dover
4.88 out of 5 average rating, 251 reviews

Mt Snow retreat, ski & summer

TimothyRating, 5 stars1 month ago
Wonderful stay in Vermont! Very spacious home with an amazing dining room and theater room in the basement ! Location was perfect for a visit to mt snow, just a few minutes away, and theater room home was cozy, 2 fireplaces , and wonderful! Recommend!!

Kid-friendly apartment rentals

Top guest favorite
The light-filled living room features a comfortable gray couch with decorative pillows, a vintage coffee table, and an eclectic mix of artwork on the walls. A television is positioned on a wooden stand, and diverse seating options are provided by antique chairs and a small dining table.
Apartment in North Adams
4.98 out of 5 average rating, 110 reviews

Charming Art Filled Apartment

AnondaRating, 5 stars6 days ago
Excellent location and decor, responsive host, off street parking, beautiful beds. Lots of art, all genres and media, an eclectic style with loads of personality. Our second time staying and we will be back again.
Guest favorite
A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.
Apartment in Wilmington
4.98 out of 5 average rating, 481 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

LisaRating, 5 stars1 week ago
Beautiful apartment in the center of Wilmington. We own land and have our camper set up in the next town over, but with the cold weather lately, the camper is still winterized. We wanted to come up and get some yard work done and stay locally, and this apartment was the clear winner! Walking distance to our favorite coffee shop, lots of restaurants, my favorite bookstore (!!) and walking trails. Loved the deck- even though it was April and iffy weather, we were able to have takeout dinner outside one night! So grateful that Jennifer allows pets, as we have two dogs and it’s often hard to find pet friendly Airbnb accommodations that are in a good location and as clean as this place! Jennifer was so kind, accommodating and responsive. She went out of her way to make sure we had a great trip- she’s definitely one of the best hosts we’ve had! Thank you for making this week wonderful! We will be back.
Top guest favorite
An open concept living area is highlighted by a comfortable light-colored sofa with decorative pillows. A dark wood coffee table centers the space, while a well-equipped kitchen features modern appliances and a light-colored island with seating. Natural light filters through the window, enhancing the inviting atmosphere.
Apartment in Brattleboro
4.9 out of 5 average rating, 360 reviews

Quiet St in Town, gardens, terrace

DavidRating, 5 stars5 days ago
We loved Jaki's apartment. It was very clean, neat, beautifully appointed, and convenient. Jaki welcomed us when we arrived and made herself available. She was friendly, warm, and very responsive. I'm returning to the area for business in the future and will book the same apartment again.
Guest favorite
A bright living area is presented with three windows allowing natural light. Two upholstered chairs and a floral-patterned sofa provide comfortable seating. A coffee table is positioned in the center, and a dining area is visible in the background, showcasing a wooden table and chairs.
Apartment in Ludlow
4.92 out of 5 average rating, 154 reviews

Great Downtown, walk to everything

MikeRating, 5 stars1 month ago
Great space, very conveniently located in town. The host was great, and would definitely stay here again
Superhost
A spacious backyard is showcased, surrounded by trees and greenery, providing a serene natural setting. A picnic table is positioned on the lawn, alongside two outdoor chairs facing a small area with a bush. The well-maintained lawn is dotted with flowers, enhancing the outdoor space.
Apartment in West Brattleboro
4.76 out of 5 average rating, 131 reviews

Cute, Convenient with Big Backyard

MichaelRating, 5 stars3 months ago
Our stay was in the cold of winter and there was ample heating in the form of radiators spread about, extra blankets, and a very powerful space heater in the living room. The artwork, furniture and layout gave a comfortable and cozy feeling. I stayed with two friends and we cooked all our meals easily with what was provided in the kitchen as far as pots, pans and utensils. During our stay John was extremely responsive and accommodating over the air bnb messages. The house is older so outlets were oddly placed with only two prongs, most of the lights were hand pull to turn on and off, and the bedroom doors locked with a hook and latch. It all felt very clean and comfortable and we were very happy with our stay.
Superhost
An open living space features a light-colored sofa with decorative pillows and a wooden coffee table. A dining area with a round table and chairs is illuminated by natural light from large windows. A bookcase and artwork add character to the room.
Apartment in Town of Rockingham
4.83 out of 5 average rating, 182 reviews

Apartment on Main Street

WinnieRating, 5 stars3 weeks ago
This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.
Guest favorite
A cozy seating area is seen with two gray armchairs adorned with decorative pillows. A small side table holds a lamp. The walls display framed art, and sunlight filters through a window covered by blinds, enhancing the inviting atmosphere.
Apartment in Whitehall
4.97 out of 5 average rating, 107 reviews

Contemporary Queen with sleeper sofa

PatrickRating, 5 stars1 month ago
Our 3rd time staying here, and it won't be our last.
Guest favorite
A one-story cabin is partially enveloped by a blanket of snow, featuring a covered porch with orange railings. The entrance is accessible via a gentle ramp, while trees in the background provide a natural setting. Soft evening light gently illuminates the cabin.
Apartment in Ludlow
4.92 out of 5 average rating, 279 reviews

Okemo Vermont Getaway

JennyRating, 5 stars1 month ago
Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

Kid-friendly condo rentals

Top guest favorite
A mudroom area features a wooden bench with decorative cushions and a slate floor. Above the bench, wooden shelves are complemented by several hooks for hanging garments or gear, creating a functional space for ski equipment and everyday items.
Condo in Ludlow
5 out of 5 average rating, 32 reviews

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6

AmberRating, 5 stars1 month ago
This was our second time staying at Lauren's beautiful home, and it certainly won’t be our last! The location is absolutely perfect—right on the mountain, making it incredibly convenient! The condo itself is beautifully appointed and stocked with everything you could possibly need for a comfortable stay. One of our favorite features was the wood-burning fireplace, which added a wonderful touch to our evenings after a long day on the slopes. Lauren is a gracious host, always attentive and ready to help with anything we needed. We recommend her place to all our family and friends and look forward to returning next year for more unforgettable memories! Thank you, Lauren, for another fantastic stay!
Guest favorite
An aerial view of a basketball court featuring two hoops, surrounded by greenery. The court is situated near a pond and is enclosed by a fence, with well-maintained grass bordering the area, providing space for outdoor activities.
Condo in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars1 month ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Top guest favorite
A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars1 month ago
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.
Guest favorite
A game room is illuminated by large windows, providing views of the greenery outside. A foosball table sits prominently, alongside a multi-sport game featuring a basketball hoop and a net for volleyball. The space encourages active play with a modern and inviting setup.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 week ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Top guest favorite
The living area features a spacious sectional sofa arranged around a coffee table, complemented by a cozy wood-burning fireplace. Natural light fills the room through large windows, which overlook the snowy landscape. A dining table for six and a media console housing a Smart TV are also present.
Condo in Stratton
4.98 out of 5 average rating, 41 reviews

Ski In/Out, Cozy 3BR Condo steps to Village

MatthewRating, 5 stars1 month ago
Exactly as described. Beautiful condo, right in the heart of Stratton. Easy ski in/ski out. Excellent proximity to everything the village has to offer. The kitchen is well equipped and the bedrooms are really comfortable. Brian was a great host! We will absolutely book again for future Stratton ski trips!
Guest favorite
A cozy dining area is highlighted by a round wooden table surrounded by black chairs. The open living room features a comfortable sofa and a decorative area rug. Soft lighting is provided by a stylish chandelier, enhancing the homey atmosphere.
Condo in Stratton
4.94 out of 5 average rating, 170 reviews

Updated Ski in/Ski out Stratton Condo!

CelesteRating, 5 stars3 weeks ago
Caitlyn An excellent host quick to respond despite moving with her babies the same day as my trip! She was accommodating and provided a clear quick easy in from my late night travel. Her space is large and spacious with great set up lighting and comfortable and clean bedding. Loved the couch bedding set up! The entrance allowed ease to store the ski stuff so roomy keeping the living space free of the typical ski vacay clutter! The bathroom shower temp and pressure with soft towel and wash cloths provided with soap, and shampoo and conditioner gave a nice end of the day relax. Plenty of blankets for layering that may be needed. Kitchen appointed well with a good stove and oven easy to use and to easy prepare with pans and utensils for cooking, plenty of silver ware and plates glasses and plates that i truly appreciated. Couldn't use the ski in/ ski out as that lift was this late int eh season but how easy was it to scoot down in 2 min! Will be my stratton stay always onward!
Superhost
A spacious sleeping area features a large bed with a textured gray coverlet, complemented by two decorative pillows. Flanking the bed are wooden nightstands with lamps. A wall art piece consisting of circular shapes adds visual interest, while natural light filters in through the nearby window.
Condo in Ludlow
4.84 out of 5 average rating, 130 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

StephenRating, 5 stars4 weeks ago
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.
Guest favorite
A wooden gate opens to a lush green lawn surrounded by trees, providing a serene outdoor space. Sunlight filters through the foliage, casting gentle shadows on the grassy area, which appears well-maintained and inviting for relaxation or play.
Condo in Stratton
4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

KatieRating, 5 stars1 month ago
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

Quick stats about vacation rentals that are kid-friendly in Winhall

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ477 before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore