We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Condo vacation rentals in Winhall

Find and book unique condos on Airbnb

Top-rated condo rentals in Winhall

Guests agree: these condos are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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.

4.99 out of 5 average rating, 121 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge. Check us out on IG for more content: @TheHandleLodge …. 18% OFF WEEKLY STAYS

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!

Charming Dover Green condo just minutes from Mount Snow Ski Resort & Lake Whitingham. This well kept 2 bedroom, 2 bathroom, plus loft bedroom features open concept living, dining, vaulted ceilings, natural woodwork, 65" TV, and a wood burning fireplace. With easy access to Mount Snow, the village of Wilmington, nearby lakes, hiking, and biking, there is so much to do for tremendous year round enjoyment. There is nearby access walkable from the unit to the public MOOver shuttle to get around town

A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 111 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

A warm gas fireplace is centrally positioned against a light-colored wall, complemented by a wood mantle and slate surround. A flat-screen TV is mounted above. A window allows natural light to brighten the area, while a desk and chair provide a workspace option.

Condo in Stratton

4.97 out of 5 average rating, 168 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

An open-concept living area is seen, featuring a fully equipped kitchen with a breakfast bar. Warm wood accents and cozy seating are highlighted, while a decorative sign with a ski theme adds character to the space. Natural light filters in through large windows.

Condo in Ludlow

4.92 out of 5 average rating, 156 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

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!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

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, 132 reviews

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

Large family friendly 1-bedroom condo with 1 King and 1 Sofa bed that is just steps away from Okemo Base lodge. Please note there is no AC at this condo complex summer time, fan will be provided. - Dedicated Xfinity modem and AP in the unit. Video conference friendly. - Free parking - Coin operated washer/dryer facilities in the building - Super quite neighborhood during Summer/Fall season, and Ski in and out in Winter season. Fireplace has been updated to electric fireplace.

The chalet duplex features a two-toned exterior with a dark wooden upper level and a white lower level. A spacious outdoor deck is visible, complemented by greenery and well-maintained shrubs, creating a serene setting within a natural landscape.

4.85 out of 5 average rating, 169 reviews

Mount Snow Close, Great Price, Lots of Room

This is a chalet duplex. You’re renting entire top 2 floors - no shared spaces. However, there’s an Airbnb rental in the lower unit of this house. Separate entrances & no indoor shared space. 2 bedrooms on the main level with a full bathroom and 2 bedrooms on the second level with a full bathroom. On site washer and dryer The kitchen comes equipped for cooking needs. ****The house has a lower level that has a 2 bedroom 1 bath Airbnb rental unit. No shared space but FYI.****

A spacious living area features light green walls and vaulted ceilings, highlighted by a large arched window. A comfortable gray sofa is paired with wooden armchairs and a coffee table. A wooden dining table is visible in the foreground, and a cozy fireplace is fitted into the wall.

Condo in Ludlow

4.78 out of 5 average rating, 194 reviews

Okemo Mountain Getaway for Families w/ Pool Access

Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

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, 124 reviews

Walk to Mt. Snow-Spa-Summer Pool

*Amenity rich studio only a 5 minute walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

An open living area features a large wooden dining table surrounded by metal chairs. The kitchen showcases modern appliances and a sleek countertop, while a comfortable seating area is arranged nearby with a sectional couch and coffee table against a textured wall.

Condo in Stratton

4.96 out of 5 average rating, 102 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.

Condo in Ludlow

4.94 out of 5 average rating, 150 reviews

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

Vacation rentals for every style

Get the amount of space that is right for you

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 condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

Top guest favorite

A spacious living area features a cozy arrangement of a grey sofa and brown leather recliner, complemented by a woven coffee table. A stone fireplace is situated against a wooden wall, with a large television mounted above. Natural light enters through window treatments.

Condo in Ludlow

5 out of 5 average rating, 32 reviews

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

A serene pond reflects the surrounding greenery and tall trees, with a distant mountain rising in the background. The clear blue sky above contributes to the tranquil setting, creating a peaceful landscape ideal for nature walks.

4.97 out of 5 average rating, 89 reviews

Cozy Mountain Condo - Let's Hike!

A spacious living room features a large sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by natural light from large windows with soft curtains. Artwork adorns the walls, creating a welcoming atmosphere.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.96 out of 5 average rating, 67 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

A street view showcases a charming area in North Adams, featuring several historic buildings with unique architecture. Prominent spires rise above the rooftops, framed by rolling hills in the background, while a clear blue sky enhances the vibrant environment.

Condo in North Adams

4.91 out of 5 average rating, 35 reviews

Downtown Condo - walk to MoCA

A snowy street is lined with charming houses, showcasing a mix of architectural styles. The backdrop features a mountain slope with visible ski trails. A clear sky with scattered clouds enhances the peaceful winter scene.

Condo in Ludlow

4.96 out of 5 average rating, 25 reviews

Perfect Getaway! Modern & Convenient to Everything

A living room features a wood-burning fireplace with an exposed brick surround, accompanied by neatly stacked firewood. A large flat-screen television is mounted above the mantle. Natural light enters through sliding glass doors, which lead to an outdoor seating area.

4.81 out of 5 average rating, 115 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

The living room features two sofas and an armchair arranged around a wooden coffee table. Natural light comes through large windows covered with blue curtains. Soft lighting is provided by two lamps, and framed artwork adorns the walls.

Condo in Stratton

4.93 out of 5 average rating, 27 reviews

Triple Tree VT 2 Level #20

Pet-friendly condo rentals

An inviting pet area features a soft, round pet bed set against a grey wall with minimalist white line art. Two food bowls sit on a wooden tray beside a ceramic container labeled 'POOP WEAVE'. Natural light fills the space, highlighting the simplicity of the design.

Condo in Bridgewater

4.95 out of 5 average rating, 22 reviews

Year-round Fun in VT: Wonderful Country Apartment

A circular seating arrangement is made with six white Adirondack chairs positioned around a metal fire pit. The grassy area is surrounded by lush greenery, and a red barn is visible in the background, alongside a propane grill on the side.

Condo in Bridgewater

4.98 out of 5 average rating, 42 reviews

Farmhouse Beauty Minutes to Woodstock & Skiing

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

Condo in Killington

4.96 out of 5 average rating, 140 reviews

Dog-Friendly Mtn Escape/AC/Pool/

A cast iron gas fireplace is centered on a stone hearth, providing warmth. A wooden ladder holds colorful blankets, while a woven basket filled with magazines is placed nearby. Light filters in through a window with horizontal blinds, enhancing the cozy ambiance.

Condo in Ludlow

4.89 out of 5 average rating, 38 reviews

Fully walkable 2BR condo in Ludlow’s village!

A cozy living room is highlighted by a comfortable sectional sofa facing a modern fireplace, adorned with seasonal greenery. A large mirror reflects natural light from the windows, and a television hangs above a wooden media console, completing the inviting ambiance.

4.97 out of 5 average rating, 30 reviews

Mt Snow Condo, 4-min Walk to Sundance Dog Friendly

A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.

4.91 out of 5 average rating, 54 reviews

Ski Condo 5 Min from Mt Snow

A two-story condo is shown with a snow-covered roof and a well-maintained exterior. A vehicle is parked in front, and snow blankets the surrounding area. The backdrop features a snow-covered mountain, displaying ski trails that contour the slopes.

Condo in Stratton

4.9 out of 5 average rating, 72 reviews

Stratton Mountain vacation spot

Condo in North Adams

4.96 out of 5 average rating, 85 reviews

Newly renovated 2BR on historic Eagle Street.

Condo rentals with a pool

A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.

4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

An indoor pool area is featured, surrounded by large windows offering views of the outdoors. Lounge chairs are arranged neatly along the poolside, and the clear water reflects the overhead lighting, creating a calming environment.

5 out of 5 average rating, 13 reviews

Cozy Updated 2 Bedroom Corner Condo

A well-maintained outdoor pool is surrounded by sun loungers, creating a serene atmosphere. Lush greenery and trees frame the background, providing a natural setting. The concrete deck features handrails for easy access, while clear skies above invite relaxation.

4.89 out of 5 average rating, 111 reviews

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

An indoor swimming pool is highlighted by large windows that allow natural light to fill the space. The pool area features a sleek, tiled edge and a set of sturdy handrails. Comfortable seating options are arranged nearby, complementing the inviting atmosphere.

4.96 out of 5 average rating, 46 reviews

Ski in/out - 2BR Condo - Indoor Pool/Spa

An indoor pool area is highlighted by a spacious swimming pool. Natural light enters through large windows, offering views of the outdoor patio. Seating areas with chairs are arranged along the walls, complemented by warm-toned curtains.

Condo in Ludlow

4.93 out of 5 average rating, 111 reviews

One Bedroom Suite Near Okemo

A welcoming entrance to Crown Point is depicted, featuring a large sign with bold lettering. The sign is framed by a wooden structure and surrounded by vibrant flowers in various colors, adding a touch of natural beauty to the landscape.

Condo in Stratton

4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

Condo in Killington

4.94 out of 5 average rating, 96 reviews

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

A cozy living area features a mix of orange and brown sofas, complemented by a wooden coffee table. A stone fireplace is positioned beneath a wooden panel wall, with a television mounted nearby. Large windows illuminate the space, offering views of the snowy outdoors.

4.7 out of 5 average rating, 10 reviews

Pool & hot tub! Hiking, nature and mountain views!

Quick stats about condo rentals in Winhall

Total rentals
30 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
590 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore