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Kid-friendly vacation rentals in Winhall

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Winhall

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

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Top guest favorite

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

4.94 out of 5 average rating, 348 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.

Cabin in Londonderry

4.95 out of 5 average rating, 194 reviews

Summit View Cottage:Winter is coming! Hot tub|3 bd

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

4.94 out of 5 average rating, 144 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.

Home in Winhall

4.87 out of 5 average rating, 183 reviews

The Mushroom House of Manchester Vermont

Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Top guest favorite

A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.

Home in Winhall

4.98 out of 5 average rating, 114 reviews

3BR 2BA Stratton Condo w/ Fireplace & Forest Views

Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and tv. Free parking. Two smart TVs & board games. Dining room table converts to a poker table.

A serene outdoor area is featured, showcasing a private heated pool surrounded by a brick patio. Lush greenery defines the background, and a rustic wooden table with chairs sits nearby, providing a space for relaxation in nature.

Chalet in Winhall

4.88 out of 5 average rating, 112 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

Top guest favorite

An open living area features a high wooden ceiling and large windows, allowing natural light to fill the space. A cozy seating arrangement is complemented by a sculptural centerpiece on a long table, with a fireplace set against a dark brick wall. Two armchairs add to the inviting atmosphere.

Chalet in Winhall

4.98 out of 5 average rating, 107 reviews

Mountain view chalet with hot tub & fire pit!

Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

Home in Winhall

4.96 out of 5 average rating, 262 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

The cabin is nestled among vibrant autumn foliage, showcasing a blend of orange, yellow, and green leaves. A gravel driveway leads up to the chalet-style house, featuring large windows that invite natural light. Surrounded by trees, the setting offers a serene retreat.

Cabin in Winhall

4.91 out of 5 average rating, 150 reviews

Snow Valley Cabin-Cozy Escape Near Skiing & Nature

The Snow Valley Cabin is a three bed one-and-a-half bath chalet-style house designed for your perfect Vermont getaway. Wooden vaulted ceilings, wood-burning fireplace, beautiful view of the snow-capped Bromley mountain, and Scandinavian style details. We are conveniently located on the edge of the Green Mountain Forest just 4 miles from Bromley, 9 miles from Stratton, 14 miles from Magic, and 12 minutes to Manchester. Stay here to relax and wind down with friends and family, and even pets!

Top guest favorite

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

5 out of 5 average rating, 251 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

An outdoor seating area features a stone pathway leading to wooden chairs arranged around a fire pit. The cabin's exterior showcases large windows and doors, framed by trees with autumn foliage, creating a welcoming ambiance.

Cabin in Londonderry

4.94 out of 5 average rating, 145 reviews

Vintage Vermont Cabin, Hot Tub, Fire Pit, Private

We can’t wait to host you at Deerwood Hill in Londonderry VT! Featured on Levi Kelly's Cabin Tours! 🌲 Deerwood Hill is a private 3.6 acre private lot 🎿 Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! 📍 Under 30 minutes to wonderful Manchester! ⛰️ 5 miles to Lowell State Park, 8 miles to Appalachian Trailhead ♥Sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Top guest favorite

The A-Frame cabin is shown nestled among trees, with a welcoming facade comprising large front windows and a sloped roof. The deck features a wooden railing and steps leading to the entrance, while snow blankets the ground, creating a serene winter atmosphere.

Cabin in Winhall

4.96 out of 5 average rating, 354 reviews

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Winhall kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

A spacious living area features a large area rug centered on natural wood flooring, with large windows allowing ample natural light. Two sectional sofas are arranged around a coffee table, creating an inviting space to relax. A stone fireplace is positioned to one side, providing a rustic touch.

Home in Windham

4.86 out of 5 average rating, 106 reviews

The Architect's Cabin, on 10 Secluded Acres

The exterior of a charming farmhouse is viewed, featuring white siding and a red front door. A large tree stands in the foreground, while green foliage and a stone path enhance the natural setting. A brick chimney is visible on the roof.

Home in Londonderry

4.94 out of 5 average rating, 175 reviews

Clean, Captivating VT Farmhouse near Stratton!

A modern living space is featured, showcasing a mid-century dining table with four black chairs. A plush gray sofa complements the wooden ceiling, illuminated by a circular pendant light. Two framed artworks hang above the sofa, adding a touch of color to the inviting room.

Home in Jamaica

4.92 out of 5 average rating, 103 reviews

The Post Haus: one-of-a-kind modern VT experience

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

4.99 out of 5 average rating, 140 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

A wide view of colorful autumn foliage is captured, showcasing a variety of trees with hues of red, orange, and yellow. A clear blue sky sets a backdrop against the distant mountains, creating a serene landscape.

4.95 out of 5 average rating, 232 reviews

Comfortable farmhouse with stunning views

Top guest favorite

The colonial home features a classic two-story facade with symmetrical windows and a central chimney. Lush green landscaping surrounds the entrance, which is accentuated by a welcoming front porch. Fall foliage decorates the yard, providing a colorful backdrop to the property.

Home in Sandgate

4.99 out of 5 average rating, 117 reviews

Country Colonial Home with rolling fields & stream

Top guest favorite

A dining area is highlighted by a wooden table set for four, surrounded by light green chairs. Natural light fills the space through two large windows, while a vintage hutch displays colorful items against a contrasting gray wall.

Home in Londonderry

4.97 out of 5 average rating, 145 reviews

Wild Blossom Farmhouse - a lovely family getaway

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

4.97 out of 5 average rating, 257 reviews

Cozy Vermont mini-house

Kid-friendly apartment rentals

An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.

Apartment in Townshend

4.93 out of 5 average rating, 243 reviews

Private Apt. on Farm, Hot Tub with views!

Top guest favorite

The exterior of a two-story house is visible, featuring a sloped roof and white siding. Lush green bushes frame the front yard, where a small decorative archway and white picket fence add charm. Surrounding trees provide a natural backdrop for the property.

Apartment in Manchester

4.99 out of 5 average rating, 262 reviews

Private two-bedroom suite within a two-story house

A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.

Apartment in Saxtons River

4.82 out of 5 average rating, 188 reviews

Apartment on Main Street

Top guest favorite

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Apartment in Andover

4.98 out of 5 average rating, 434 reviews

Private Hilltop farm apartment

Top guest favorite

A two-story, white wooden house is surrounded by lush greenery and shrubs. A porch with a small seating area is visible, along with an air conditioning unit installed on the upper level's front wall. The bright sky and soft clouds provide a picturesque backdrop.

Apartment in Poultney

4.94 out of 5 average rating, 355 reviews

Cozy Poultney Village Apartment

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Apartment in Putney

4.97 out of 5 average rating, 102 reviews

Minimal organic hideaway inspired by nature

Top guest favorite

A large Victorian house is framed by vibrant autumn foliage, with colorful orange, yellow, and red leaves. The home features a spacious porch and multiple gabled roofs, blending harmoniously with the surrounding nature and the peaceful landscape.

Apartment in North Adams

4.97 out of 5 average rating, 584 reviews

Steps to MoCA: 2bd + SAUNA!

The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.

Apartment in Middletown Springs

4.89 out of 5 average rating, 259 reviews

Apartment in Vermont Historic Home

Kid-friendly condo rentals

A welcoming living area features exposed wood beams on the ceiling and a stone fireplace. A flat-screen television is mounted on the wall beside wooden shelves displaying local artwork. A dark sectional sofa is complemented by decorative pillows, and natural light filters through the windows.

Condo in Ludlow

4.95 out of 5 average rating, 201 reviews

Exceptional Village Fireplace Condo On Shuttle Rte

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.

4.87 out of 5 average rating, 241 reviews

Mt Snow Ski In/Out at Seasons

Top guest favorite

A modern living room corner features a brown leather recliner with high backrest beside a window. A small table holds a potted plant, while a wood stack is positioned against the wall for a rustic touch. Natural light filters through brown curtains.

4.99 out of 5 average rating, 121 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

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, 131 reviews

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

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, 174 reviews

Updated Ski in/Ski out Stratton Condo!

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Condo in Stratton

4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.

4.84 out of 5 average rating, 121 reviews

Walk to Mt. Snow-Spa-Summer Pool

Top guest favorite

The exterior showcases a two-story condo surrounded by greenery. A pathway lined with gravel leads to the entrance. Flowering plants and shrubs are visible along the pathway, and a lamp post adds a lighted accent. The condo features a mix of dark and muted colors with a welcoming porch.

4.92 out of 5 average rating, 128 reviews

3 Story Condo - 5 Minutes to Mount Snow!

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

Total rentals
80 properties
Nightly prices starting at
G$35,579 GYD before taxes and fees
Total number of reviews
3.1K 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

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