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Family-friendly vacation rentals in Winhall

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 220 vacation rentals in Winhall

  • Nightly prices starting at

    Winhall vacation rentals start at ﺩ.ﺇ 477 per night before taxes and fees

  • Verified guest reviews

    Over 7,090 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    220 of Winhall vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winhall rentals

  • 4.9 Average rating

    Winhall stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Winhall

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

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Guest favorite
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, 260 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

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

KitchenFamilyRiver

Guest favorite
A rustic cabin built on stilts is surrounded by snow-covered ground and tall trees. The structure features a pitched roof and a spacious deck. Sunlight filters through the branches, casting shadows on the snow, highlighting the natural beauty of the winter landscape.
Cabin in Winhall
4.88 out of 5 average rating, 111 reviews

Chic Cabin with Fireplace at Stratton Mountain

Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington

FamilyKitchenView

Guest favorite
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
4.95 out of 5 average rating, 350 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

FamilyIndoor spacesGetting around

Top guest favorite
The chalet is positioned on a gently sloping grassy area, featuring a spacious deck with a hot tub and several outdoor seating options arranged around a fire pit. Large windows reflect warm interior light, framing a serene natural backdrop of trees, enhancing the inviting ambiance.
Chalet in Winhall
4.99 out of 5 average rating, 136 reviews

Mountain view chalet with hot tub & fire pit!

Welcome to the @vermontviewchalet! 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.

Indoor spacesFamilyWifi

Top guest favorite
A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.
Chalet in Londonderry
4.95 out of 5 average rating, 128 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

FamilyKitchenParks

Guest favorite
An aerial view showcases a cabin with a wooden exterior and a sloped roof. A spacious deck is furnished with several chairs surrounding a fire pit. Beside the deck, a hot tub is nestled among the trees, highlighting the cabin's serene outdoor setting.
Cabin in Londonderry
4.95 out of 5 average rating, 187 reviews

Idyllic Cabin in VT, Hot Tub, Fire Pit, Charm

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 4 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

FamilyKitchenSkiing

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, 166 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 smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Indoor spacesFamilyBathroom

Guest favorite
A charming log cabin is surrounded by vibrant autumn foliage, showcasing a dark wooden exterior and a sloped green roof. The mountains in the background provide a scenic view, enhancing the peacefulness of the property, which is set on a gravel driveway.
Cabin in Sunderland
4.99 out of 5 average rating, 157 reviews

The Birchwood Cabin - Stunning Mountain Views

Welcome to the Birchwood Cabin - a beautiful log cabin with stunning mountain views! Relax in the hot tub overlooking the mountains or enjoy hot chocolate by the fire. Play a game of pool or shuffleboard downstairs. The Birchwood Cabin is in a peaceful, quiet location but is only a 10-minute drive to Manchester, if you'd like to go shopping or grab a bite to eat! Hit the slopes at Bromley Mountain or Stratton Mountain or in the warmer weather head to The Equinox for a round of golf!

Indoor spacesKitchenNearby

Guest favorite
An aerial view showcases the expansive outdoor deck of the Shred Shack, featuring a hot tub and a large dining table for outdoor meals. Sun loungers are positioned nearby, and the building's blue exterior offers a vibrant contrast with the surrounding greenery.
Home in Winhall
4.95 out of 5 average rating, 110 reviews

Shred Shack: A/C | Hot Tub | Sauna | EV charger

Escape to the Shred Shack by 42 North LP, your ultimate mountain escape in Vermont! The Shred Shack offers stunning mountain & valley views from its expansive great room. Relax & recharge by the grand fireplace, in the private indoor sauna, or the mountain-view hot tub. Entertain effortlessly in the open-concept kitchen, dining, and living area – perfect for memorable meals & gatherings. Kids will love the unique indoor swing! Your perfect blend of adventure and comfort awaits!

KitchenFamilyWalkability

Top guest favorite
The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.
Cabin in Townshend
4.96 out of 5 average rating, 202 reviews

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

KitchenIndoor spacesAmenities

Top guest favorite
Cabin in Winhall
4.96 out of 5 average rating, 389 reviews

Dog Friendly A-Frame Retreat near Hiking, Dining

Escape to The Vermont A-Frame, our dog-friendly retreat on the edge of Green Mountain National Forest! This cozy 1965 cabin comfortably sleeps 4 and is perfect for skiers, hikers, or those seeking relaxation. Features a stone fireplace, dedicated workspace with fast WiFi, and a fire pit. Your ideal base for exploring Southern Vermont's natural beauty and charming towns. Find us @thevermontaframe!

Indoor spacesFamilyLocation

Top guest favorite
The exterior of a modern home is framed by lush greenery, featuring a dark wooden structure with large windows. A front entrance is highlighted by wooden steps leading to the door, while a gravel path borders the property.
Chalet in Winhall
4.96 out of 5 average rating, 104 reviews

Minutes to Stratton! Large, private home w. sauna

Your dream ski vacation awaits! Less than 2 miles to Stratton Mountain access road; 15 minutes to Bromley; 15 min to Manchester Ctr; 30 min to Mt Snow. With three levels, your group can really spread out: 4 bedrooms + bonus room, 4 full baths, open kitchen, living room with a fireplace, loft area, sauna, and laundry. Monthly discount available. Ski Shuttle for rentals of 30+ days.

Indoor spacesFamilyBathroom

Popular amenities for Winhall family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 776 reviews

Schoolhouse Spa Retreat on a Vermont Farm

FamilyIndoor spacesView

Top guest favorite
Tiny home in Ludlow
4.96 out of 5 average rating, 108 reviews

Alpine Reflection + Hot Tub

Indoor spacesKitchenHeating

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 395 reviews

Beautiful Timber Frame Retreat

FamilyKitchenComfort

Top guest favorite
Cabin in Shaftsbury
4.99 out of 5 average rating, 327 reviews

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub

KitchenFamilyWalkability

Superhost
The treehouse stands illuminated at dusk, showcasing its wooden structure and spacious porch. Soft light spills from the windows, creating a warm glow that contrasts with the evening sky. Decorated flower pots add a touch of color to the surrounding area.
Treehouse in Londonderry
4.8 out of 5 average rating, 103 reviews

Kloki - River Lovers Treehouse - sauna & hot tub!

FamilyIndoor spacesNearby

Top guest favorite
The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.
Cabin in Landgrove
4.99 out of 5 average rating, 219 reviews

The Owl’s Nest in Landgrove

Indoor spacesKitchenNearby

Top guest favorite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Apartment in Londonderry
4.96 out of 5 average rating, 617 reviews

Vermont Getaway Apartment

KitchenFamilySleep quality

Guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 151 reviews

Vermont Mirror House

KitchenIndoor spacesGrill

Family- and pet-friendly home rentals

Superhost
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
4.85 out of 5 average rating, 203 reviews

The Mushroom House of Manchester Vermont

FamilyIndoor spacesComfort

Top guest favorite
Cabin in Stratton
5.0 out of 5 average rating, 199 reviews

Log Cabin King Beds AC Near Hike Bike Swim Golf!

KitchenFamilyTV

Top guest favorite
The A-frame house is framed by tall trees, featuring large triangular windows that enhance natural light. A wooden deck extends to a seating area with two rocking chairs and a picnic table. A person walks their dog along the path leading to the entrance.
Place to stay in Stratton
4.99 out of 5 average rating, 218 reviews

The Chal-A-Frame Vermont

Indoor spacesKitchenSleep quality

Top guest favorite
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, 151 reviews

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

FamilyIndoor spacesWifi

Top guest favorite
A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.
Bus in Granville
4.9 out of 5 average rating, 207 reviews

Serene Bus Getaway Among Rolling Farm Land

KitchenFamilyDecor

Top guest favorite
The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.
Home in Weston
4.95 out of 5 average rating, 321 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Indoor spacesKitchenCondition

Top guest favorite
The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.
Tiny home in Dover
5.0 out of 5 average rating, 221 reviews

Rustic Cabin in foothills of Green Mountains

FamilyKitchenView

Top guest favorite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica
4.99 out of 5 average rating, 108 reviews

Designer Chalet w/ Mountain Views close to it all

Indoor spacesKitchenDecor

Family-friendly home rentals with a pool

Top guest favorite
A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.
Barn in Newfane
4.98 out of 5 average rating, 175 reviews

Beautiful rustic woods and fields retreat.

KitchenIndoor spacesValue

Top guest favorite
A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.
Condo in Stratton
4.96 out of 5 average rating, 177 reviews

Cozy condo within walking distance to the slopes.

KitchenFamilyDecor

Guest favorite
A rustic log cabin features a porch with seating arrangements, including Adirondack chairs. The front yard is partially landscaped with small plants. Stacked firewood is visible next to the cabin, and the structure is surrounded by trees and greenery, providing a natural, secluded setting.
Cabin in Wardsboro
4.8 out of 5 average rating, 275 reviews

Log Cabin Near Stratton/Mt Snow

KitchenFamilyLocation

Top guest favorite
A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.
Farm stay in Clarendon
5.0 out of 5 average rating, 108 reviews

Dream Catcher Farm

FamilyIndoor spacesGetting around

Top guest favorite
Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.
Cottage in Newfane
4.99 out of 5 average rating, 293 reviews

Cozy Vermont Antique Sugar House with Fireplace

FamilyKitchenTV

Top guest favorite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville
4.91 out of 5 average rating, 1012 reviews

Moon Valley Country Retreat no clean fee pets yes

Indoor spacesFamilyPool

Top guest favorite
A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.
Cottage in Wardsboro
4.97 out of 5 average rating, 110 reviews

Modern Cottage between Stratton and Mount Snow VT

FamilyKitchenQuiet

Guest favorite
The cozy interior features exposed wooden beams and warm lighting. A spacious bed is positioned alongside a sitting area with a sofa and chairs. A braided rug adds texture to the rustic floor, while windows invite natural light into the inviting space.
Tiny home in Brattleboro
4.93 out of 5 average rating, 127 reviews

“Elm” Cozy Pond-side Cabin w/wood stove

FamilyKitchenShared spaces

When is the best time to visit Winhall?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 2,464ﺩ.ﺇ 2,666ﺩ.ﺇ 1,924ﺩ.ﺇ 1,304ﺩ.ﺇ 1,183ﺩ.ﺇ 1,212ﺩ.ﺇ 1,271ﺩ.ﺇ 1,304ﺩ.ﺇ 1,205ﺩ.ﺇ 1,447ﺩ.ﺇ 1,469ﺩ.ﺇ 2,347
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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