Family-friendly holiday rentals in Winhall

5 out of 5 average rating, 199 reviews

Cabin in Stratton

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Indoor spacesKitchenNearby

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.

4.85 out of 5 average rating, 203 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.

Indoor spacesFamilySkiing

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.

4.95 out of 5 average rating, 352 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 spacesEV charging

4.99 out of 5 average rating, 136 reviews

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

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 spacesFamilyBathroom

4.95 out of 5 average rating, 187 reviews

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

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

FamilyKitchenAccuracy

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.

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.

FamilyIndoor spacesCleanliness

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.

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!

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 777 reviews

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

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

KitchenIndoor spacesBiking

4.96 out of 5 average rating, 390 reviews

Cabin in Winhall

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 spacesKitchenParks

4.96 out of 5 average rating, 104 reviews

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

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.

KitchenFamilyBeach

A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.

4.98 out of 5 average rating, 430 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

KitchenIndoor spacesLocation

4.94 out of 5 average rating, 132 reviews

A modern cabin is set amidst lush greenery, elevated on stilts for an unobstructed view. The exterior features a mix of wood and dark finishes, with large windows allowing natural light to fill the interior. A gravel path leads to the entrance.

Home in Jamaica

The Post Haus - One-of-A-Kind Modern VT Experience

Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!

FamilyKitchenQuiet

Popular amenities for Winhall family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 171 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 158 reviews

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

The Birchwood Cabin - Stunning Mountain Views

KitchenIndoor spacesQuiet

4.99 out of 5 average rating, 220 reviews

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

The Owl’s Nest in Landgrove

FamilyKitchenLong stay

4.99 out of 5 average rating, 397 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

KitchenFamilyCondition

4.96 out of 5 average rating, 172 reviews

Chalet in Stratton

HYGGE HOUSE Luxe HotTub, Sauna, Summer/Fall Leaves

Indoor spacesKitchenHiking

4.95 out of 5 average rating, 152 reviews

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

Vermont Mirror House

Indoor spacesFamilyQuiet

4.96 out of 5 average rating, 619 reviews

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

Vermont Getaway Apartment

Indoor spacesKitchenSolo travel

4.95 out of 5 average rating, 110 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

KitchenFamilySleep quality

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 144 reviews

The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.

Chalet in Wilmington

Snug Chalet - Wi-Fi + Close to Mount Snow

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 151 reviews

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

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

FamilyIndoor spacesCondition

4.94 out of 5 average rating, 1,376 reviews

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

Indoor spacesFamilyView

4.99 out of 5 average rating, 108 reviews

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

Designer Chalet w/ Mountain Views close to it all

Indoor spacesFamilyCleanliness

4.95 out of 5 average rating, 128 reviews

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

10 min from Stratton! Log Cabin w/ Beautiful Views

Indoor spacesFamilyHiking

5 out of 5 average rating, 131 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

FamilyKitchenValue

4.85 out of 5 average rating, 635 reviews

A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.

Cottage in Jamaica

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

FamilyIndoor spacesCleanliness

4.98 out of 5 average rating, 123 reviews

A deck area features four comfortable chairs surrounding a glass-topped table. Lush greenery and trees with autumn foliage create a colorful backdrop, while a clear blue sky adds to the inviting outdoor setting.

Barn in Manchester

Cozy Barn home w/ Mountain Views

KitchenFamilyHiking

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 211 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Magical Farm Getaway - a must visit!

Indoor spacesFamilyAir conditioning

4.8 out of 5 average rating, 276 reviews

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

Log Cabin Near Stratton/Mt Snow

Indoor spacesFamilyParks

4.9 out of 5 average rating, 108 reviews

A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.

Condo in Stratton

~10% OFF~Walk To Mountain~Amenities

FamilyIndoor spacesShared spaces

4.92 out of 5 average rating, 221 reviews

A rustic log cabin is set amidst lush greenery, framed by tall trees. A covered porch extends along the front, providing space for seating. Natural stone steps lead up to the entrance, and a small fire pit is visible in the foreground, surrounded by stones.

Cabin in Wardsboro

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

FamilyIndoor spacesBarbecue

4.91 out of 5 average rating, 1,015 reviews

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

Moon Valley Country Retreat no clean fee pets yes

KitchenFamilyEV charging

5 out of 5 average rating, 109 reviews

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

Dream Catcher Farm

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 176 reviews

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

Beautiful rustic woods and fields retreat.

KitchenIndoor spacesAccess