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Ski-in/Ski-out vacation rentals in Winhall

Find and book unique ski-in/ski-out homes on Airbnb

Quick stats about vacation rentals that are ski-in ski-out in Winhall

  • Total vacation rentals

    Explore 20 vacation rentals in Winhall

  • Nightly prices starting at

    Winhall vacation rentals start at ﺩ.ﺇ 551 per night before taxes and fees

  • Verified guest reviews

    Over 620 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 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 ski-in/ski-out rentals in Winhall

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.
Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay

4.9 out of 5 average rating, 184 reviews
Top guest favorite
A cozy bedroom features a spacious bed draped in a soft, dark blanket. The walls are adorned with a captivating array of framed artwork, showcasing various styles. A bedside table holds a lamp, and a curtain partially covers a window, allowing natural light to filter in.
Place to stay in North Adams

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

4.94 out of 5 average rating, 279 reviews
Guest favorite
Condo in Dover

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

4.92 out of 5 average rating, 128 reviews
Superhost
A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.
Home in Wilmington

MtSnow HotTub Pool Table AirHockey PingPong *Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

4.85 out of 5 average rating, 144 reviews
Guest favorite
A spacious living area is depicted with a large sectional sofa and a wooden coffee table. A stone fireplace serves as a focal point, featuring a mounted TV above. Natural light streams through the windows, illuminating bookshelves filled with games and books, while a stack of firewood is neatly arranged beside the fireplace.
Condo in Dover

Slopeside @ Seasons on Mount Snow (Ski-In/Out)

⌲ Escape to Seasons on Mount Snow & stay in our fully equipped 3 bedroom condo where you can you can ski-in & out directly from the condo building! ⌲ Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities which include a gym, pool, hot tub, sauna & fire pit. ⌲ Spring thru fall activities in the area include hiking, biking, tennis & pickleball (at Seasons), scenic rides, lakes, golf, camp, spa & enjoying the stunning fall colors.

4.92 out of 5 average rating, 105 reviews
Guest favorite
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.
Condo in Dover

Great Amenities-Season Condo gym-sport center-pool

True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

4.94 out of 5 average rating, 107 reviews
Top guest favorite
A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.
Home in Cavendish

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

5.0 out of 5 average rating, 136 reviews
Top guest favorite
A spacious living area features a rustic stone fireplace and a large, comfortable leather sofa arranged around a wooden coffee table. Large windows invite natural light, while a textured area rug adds warmth to the wooden flooring. Decorative elements include a chandelier and wall signage.
Home in Stratton

Stratton walk on/ski off, Kings, hot tub, shuttle

Perfect spot for year round relaxation! Located on Stratton Mountain this townhome has everything you could want. • 4 bedrooms • 4 full bathrooms (bathroom on every floor!) • Sleeps 10 across 7 beds (3 King and 2 sets of twin bunks) • 2 living areas • Hot tub • Shuttle • Walk to trails! ~400 yard walk • Ski nearly all the way home! ~50 yard walk • 5 min to Pikes Falls swimming hole • 18 min to Bromley • 25 min to Manchester PLEASE NOTE: Ski on/off is snow/weather dependent!

5.0 out of 5 average rating, 28 reviews
Top guest favorite
Cabin in Peru

The Grateful Barn

THE GRATEFUL BARN is a SW Vermont classic. Renovated 1800's Vermont barn. Located on a National Forest Rd. & land locked by the entire Green National Forest The home is a cozy converted barn located next to a seasonal country home. The Barn offers a private bedroom with a queen sized bed, 2 single beds in a loft area & a pull out double bed in living room. This remote VT location is steps from the Long Trail, 7 minute drive to Bromley & 20 minutes to Stratton or Magic MT.

4.83 out of 5 average rating, 120 reviews
Top guest favorite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

4.9 out of 5 average rating, 242 reviews
Guest favorite
A spacious living area includes a large sectional sofa, a wooden dining table with chairs, and a flat-screen TV mounted above a fireplace. Natural light filters in through a large window, illuminating the soft beige walls and neutral carpeting.
Apartment in Stratton

Summit’s Stratton Sneak Away II

Come enjoy the convenience of this cozy one bedroom, with fireplace located adjacent to the village and lifts at Stratton Mountain. Walk to lifts, shopping and dining. 3 hot tubs and a pool open year round, with a sauna. The condo also features a spacious living area, a flat screen TV, and a pull out full size sofa bed. The unit has WiFi, DVD player, and cable TV. Washer and Dryer across the hall, locker to store your gear and free underground heated parking.

4.91 out of 5 average rating, 32 reviews
Guest favorite
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

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!

4.97 out of 5 average rating, 120 reviews

Popular amenities for Winhall ski-in/ski-out rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Ski-in/ski-out house rentals

Guest favorite
Home in Dummerston

The Sugarhouse

4.96 out of 5 average rating, 133 reviews
Guest favorite
The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.
Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.92 out of 5 average rating, 114 reviews
Guest favorite
A spacious open-plan living area features a large brown sofa alongside a comfortable leather recliner. Light blue walls are adorned with vintage ski decor. A coffee table sits centrally on a patterned rug, and a dining bar with seating overlooks the kitchen area equipped with modern amenities.
Home in Ludlow

1st floor, Okemo contemporary country 3 BR 2 BA

4.88 out of 5 average rating, 155 reviews
Top guest favorite
Home in Stratton

Village Watch Ski-in/out Condo in Stratton, VT

5.0 out of 5 average rating, 12 reviews
Top guest favorite
A modern chalet is set among snow-covered trees, featuring a spacious deck with a railing. Dark blue exterior walls contrast with white snow, while large windows provide views of the surrounding winter landscape. The sloped roof is lined with fresh snow, enhancing the serene atmosphere.
Home in Londonderry

Modern Chalet: Magic Mountain

5.0 out of 5 average rating, 41 reviews
Guest favorite
A cozy living area is illuminated by ambient lighting from a fireplace and table lamps. A television is mounted on the wall, while comfortable leather sofas face a wooden coffee table. Large windows reveal softly draped curtains and a gentle glow from a nearby table lamp.
Home in Stratton

Vintage Vermont

5.0 out of 5 average rating, 18 reviews
Superhost
Home in Stratton

SnowBridge Stratton Ski in/Out Trailside 4 Bdrm

4.8 out of 5 average rating, 10 reviews
Top guest favorite
A charming front porch is displayed with seating arrangements that include a cozy sofa. The white exterior is complemented by wooden beams and decorative lights, while seasonal decorations, like corn stalks, add character. A vibrant landscape frames the home.
Home in Wilmington

Farmhouse With Large Game Room, Walk to Downtown

4.98 out of 5 average rating, 62 reviews

Family-friendly, ski-in/ski-out home rentals

Guest favorite
A clear blue swimming pool is surrounded by a paved deck featuring several lounge chairs. In the backdrop, a multi-level lodge with dark siding and white trim is set against a backdrop of green trees and a blue sky.
Condo in Peru

Summer in the mountains!

4.98 out of 5 average rating, 98 reviews
Guest favorite
A cozy living area is illuminated by a gas fireplace, with a media console mounted above. A spacious sofa and wooden coffee table offer a comfortable seating arrangement. A bar-height dining area with stools is visible in the background, along with a work desk and ample natural light.
Apartment in Stratton

Renovated Long Trail 1 Bedroom

4.97 out of 5 average rating, 34 reviews
Top guest favorite
The spacious great room features a stone fireplace, providing a focal point for relaxation. Comfortable seating is arranged invitingly, with a wooden coffee table at the center. Large windows are adorned with light-filtering curtains, allowing soft natural light to enter, while a dining area is visible in the background.
Condo in Stratton

Great Ski In / Ski Out Location!

5.0 out of 5 average rating, 31 reviews
Top guest favorite
Townhouse in Winhall

Mountain Haven for Families| Deck | Shuttle

5.0 out of 5 average rating, 24 reviews
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

Ski In/Out, Cozy 3Bed condo steps to Village

4.98 out of 5 average rating, 58 reviews
Guest favorite
Apartment in Stratton

Walk to Ski Lifts & Village | Hot Tub & Sauna

4.89 out of 5 average rating, 9 reviews
Guest favorite
A wooden dining table is set for a meal, surrounded by several wooden chairs. A spiral staircase leads to the upper level. Ski equipment is mounted on the wall, and a comfortable seating area is visible in the background, with a relaxed atmosphere created by soft furnishings.
Townhouse in Peru

The Best Vermont Has to Offer!

4.74 out of 5 average rating, 35 reviews
Superhost
A modern kitchen is equipped with stainless steel appliances, including a refrigerator, oven, and microwave. White cabinetry contrasts with dark granite countertops, while a tile backsplash adds subtle texture. Warm wood flooring complements the overall design, creating a functional and inviting cooking space.
Townhouse in Stratton

Ski In / Ski Out 4BR / 3BA Private Hot Tub and sha

4.78 out of 5 average rating, 54 reviews

Ski-in/ski-out cabin rentals

Guest favorite
The chalet is showcased amidst vibrant autumn foliage, with large windows allowing natural light to fill the space. A spacious deck with a wooden railing extends from the upper level, while the surrounding trees maintain a tranquil setting.
Cabin in Londonderry

Green Mt Magic - Close to Golfing Tennis Parks

4.88 out of 5 average rating, 104 reviews
Superhost
The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.
Cabin in Cavendish

The Cozy Little Red Cabin

4.94 out of 5 average rating, 182 reviews
Superhost
An inviting interior space features wood-paneled walls and ceiling. A cozy dining area with a round table and two chairs is seen, along with a pair of armchairs near a rustic wood stove. A ladder leads to a loft, while sunlight streams through multiple windows.
Cabin in Londonderry

The Run-In - Beautiful Country Cabin with Hot Tub

4.66 out of 5 average rating, 473 reviews
Superhost
A spacious interior showcases warm wooden floors and a cozy wood-burning stove at the center. Soft lighting from multiple pendant lamps creates a welcoming ambiance. A dining area with a wooden table and chairs is visible, and rustic details can be seen in the surrounding decor.
Cabin in Londonderry

Beautiful Art Studio with hot tub/sauna #1 Airbnb

4.75 out of 5 average rating, 437 reviews

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