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Ski-in/Ski-out holiday rentals in Windsor County

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Top-rated ski-in/out rentals in Windsor County

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

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Top guest favourite
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.

ValueFamilyCheckout

5.0 out of 5 average rating, 136 reviews
Top guest favourite
A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.
Apartment in Killington

Alpine Condo - Close to Ski, Golf & Bike

Updated 1-bedroom condo with stylish alpine feel in the heart of Killington! Just minutes from the ski slopes, Bike Park, Adventure Center, golf, hiking, and scenic drives. ⛷️🚴🏻‍♂️🍂 Enjoy Vermont’s spectacular fall foliage, winter adventures, or a relaxing mountain getaway. After a day outdoors, cozy up by the gas fireplace. Sleeps 4 with king bed + queen pullout. Ski Shuttle available weekends (Dec–April) & ski home trail. Pack & Play available upon request. Reg #007718

FamilyLocationDecor

4.99 out of 5 average rating, 186 reviews
Top guest favourite
A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.
Tiny home in Hartland

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

ValueFamilyLayout

4.97 out of 5 average rating, 244 reviews
Guest favourite
Apartment in Killington

3BR at base of Pico Mountain! Book your Fall Stay!

Ski-on/Ski-off!! Our condo is at the base of Pico Mountain and offers amazing views from the private balcony. Enjoy all the benefits of being slope side of Pico Mountain while just 10 minutes away from Killington Resort! Pico Mountain offers 57 trails with 6 lifts and is a family-favorite to avoid some of the weekend crowds at Killington. Less then 1 mile from the Long Trail and Deer Leap overlook hiking trail. Both fantastic must-do hikes when in the area!

ValueLocationBiking

4.93 out of 5 average rating, 124 reviews
Guest favourite
Home in Killington

Golf and Mountain Biking outside the door!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

LocationFamilyComfort

4.89 out of 5 average rating, 141 reviews
Guest favourite
A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.
Chalet in Killington

Large Chalet; Sauna, Hot Tub; Walk to Trail

Short walk (200 yds) to Homestretch ski trail at Killington ski mountain. Trail is weather dependent, from late Dec to mid-March. If the nearby trail is not open, it will not be available. Close to hiking/biking trails, golf, nightlife, rivers and lakes. Large open living space and lots of sleeping space makes our home comfortable for large groups. Driveway holds up to 5 cars. Enjoy relaxing in the hot tub, sauna or spending time by the fire.

FamilyLocationGrill

4.86 out of 5 average rating, 265 reviews
Guest favourite
A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.
Apartment in Killington

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

Your four-season basecamp at Mountain Green Resort — walk to the lifts for skiing or summer mountain biking, plus hiking and golf nearby. This renovated 1-bedroom sleeps 4, with a reserved garage parking spot and a winter shuttle to Snowshed every 15 min. Enjoy a renovated kitchen, Wi-Fi, and smart TVs. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool Memorial Day–mid-September.

LocationValueWalkability

4.91 out of 5 average rating, 227 reviews
Top guest favourite
A tranquil scene captures a log cabin nestled by a pond, surrounded by trees. The clear water reflects the cabin and vibrant foliage, creating a serene atmosphere. Tall grasses frame the pond's edge, while the landscape showcases the lush greenery of Vermont.
Cabin in South Royalton

Cozy 4-season Cabin on Pond - "East Cabin"

Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.

FamilyLocationHospitality

4.96 out of 5 average rating, 241 reviews
Top guest favourite
Apartment in Killington

Ski-In/Out, Hot Tub, Pet-Friendly

Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.

FamilyLocationLaundry

4.95 out of 5 average rating, 182 reviews
Top guest favourite
A cozy bedroom features a spacious king bed dressed in a plaid blanket, complemented by decorative pillows. Two bedside lamps provide soft illumination. A wood shelf above the bed holds decorative items. A large window offers a view of the outdoors, dressed with light curtains.
Home in Killington

CozyDen - AC, Bike to Mountain, Porch!

Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!

FamilyLocationAmenities

4.98 out of 5 average rating, 219 reviews
Top guest favourite
A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.
Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.

ValueFamilyKitchen

4.97 out of 5 average rating, 157 reviews
Guest favourite
A cozy cabin with a crisp wooden exterior is located amidst lush greenery and trees. A serene pond is visible nearby, with a flower farm and several outbuildings in the background. Expansive fields lead towards the picturesque landscape of mountains under a cloudy sky.
Cabin in Bethel

The Gourmet Cabin at Stitchdown Farm

Take a vacation from your problems in this spacious & cozy cabin on a working flower farm in the mountains. Nestled next to the flower fields and central on our 260 acres of pasture and forest with walking/skiing trails throughout, the Gourmet Cabin is a place to take a break from the bullshit and melt into the Vermontness of it all.

LocationFamilyCheckout

4.95 out of 5 average rating, 114 reviews

Popular amenities for Windsor County ski-in/out rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Ski-in/out house rentals

Guest favourite
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

FamilyLocationGrill

4.88 out of 5 average rating, 155 reviews
Guest favourite
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

FamilyLocationAir conditioning

4.92 out of 5 average rating, 114 reviews
Guest favourite
Home in Hartford

Renovated Kingswood 3Br | Pool, Golf, Club Access

LocationValueLayout

5.0 out of 5 average rating, 15 reviews
Guest favourite
The living area features a combination of plush seating, a wooden coffee table, and large windows offering views of the surrounding trees. A dining area is visible, accompanied by a stylish chandelier and open kitchen access. Rich wooden beams adorn the ceiling, enhancing the space's rustic charm.
Home in Killington

The Slippery Slope Chalet: Ski-In/Ski-Out Pico

FamilyLocationKitchen

4.83 out of 5 average rating, 29 reviews
Guest favourite
A cozy living area features a wood fireplace flanked by a comfortable leather couch and a decorative chair. A rustic dining table complements the space, while large windows provide ample natural light and views of the surrounding woods. A flat-screen TV is mounted above the fireplace.
Home in Killington

Killington Condo Near Mountain Biking Trails

LocationFamilyIndoor spaces

4.94 out of 5 average rating, 63 reviews
Top guest favourite
A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.
Home in Ludlow

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

FamilyLocationSkiing

4.95 out of 5 average rating, 43 reviews
Top guest favourite
A spacious living area is highlighted by a cozy wood-burning fireplace, complemented by comfortable seating and warm earthy tones. A rustic coffee table sits in front of a sectional sofa, with a view towards an open kitchen area, creating a welcoming atmosphere.
Home in Killington

Ski On/Off Sunrise at Killington

ValueFamilyAccess

5.0 out of 5 average rating, 26 reviews
Superhost
Home in Killington

The Navillus House: Hot Tub, Slopeside, Ski On/Off

FamilyValueRiver

4.71 out of 5 average rating, 24 reviews

Family-friendly, ski-in/out home rentals

Guest favourite
Chalet in Killington

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

ValueFamilyCheck-in

4.84 out of 5 average rating, 264 reviews
Top guest favourite
A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.
Apartment in Killington

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

LocationValueAccess

4.94 out of 5 average rating, 112 reviews
Guest favourite
A cozy living space features a large window providing natural light. A comfortable couch and chair are positioned around a coffee table. The room includes a spacious bed with a blue and black patterned blanket, while a 50-inch TV is mounted on the wall.
Apartment in Killington

Killington-Pico ski in/out Studio at base of Pico

LocationValueQuiet

4.89 out of 5 average rating, 270 reviews
Guest favourite
The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.
Apartment in Ludlow

Winterplace - Steps away from Slopes

ValueLocationIndoor spaces

4.96 out of 5 average rating, 116 reviews
Guest favourite
Chalet in Stockbridge

Private Mountain Sanctuary | 15 Min to Killington

ValueFamilyAmenities

4.92 out of 5 average rating, 51 reviews
Guest favourite
Apartment in Ludlow

Ski-In/Out Condo on Okemo Mountain

LocationFamilyCleanliness

4.92 out of 5 average rating, 26 reviews
Top guest favourite
A recently renovated kitchen features stainless steel appliances, including a refrigerator and microwave. Light gray cabinetry complements a tiled backsplash. A dining table is positioned under a ceiling light, surrounded by chairs, with a decorative bowl atop the table.
Apartment in Ludlow

Bus On-Bus Off Two Bedroom Condo

FamilyLocationComfort

4.96 out of 5 average rating, 51 reviews
Top guest favourite
A warm living area features a stone fireplace as the focal point, complemented by wooden beams and walls. A gray sofa and a red armchair invite relaxation, while a wooden coffee table holds a stack of magazines. Large windows allow natural light to fill the space.
Chalet in Ludlow

Five Bedroom Family Home on Okemo with A.C. splits

FamilyValueBack garden

4.98 out of 5 average rating, 45 reviews

Ski-in/out cabin rentals

Top guest favourite
Cabin in Peru

The Grateful Barn

ValueFamilyCleanliness

4.83 out of 5 average rating, 120 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

ValueLocationDecor

4.75 out of 5 average rating, 437 reviews
Superhost
The cabin features a traditional A-frame design with a green metal roof, set against a backdrop of snow-covered ground and surrounding evergreen trees. Large windows offer ample natural light, while a clear path leads to the entrance. A logo indicating ski access is visible in the foreground.
Cabin in Killington

SKI ON/OFF Spruce Glen Cabin 1 AC Fireplace Sauna

LocationConditionCleanliness

Top guest favourite
A spacious log cabin is set amidst lush greenery, featuring a welcoming porch and multiple windows that allow natural light to fill the interior. The well-maintained lawn offers a peaceful atmosphere, with trees surrounding the property, enhancing the sense of seclusion.
Cabin in Mendon

THE CABIN....a Vermont log home

LocationValueBathroom

4.85 out of 5 average rating, 254 reviewsA spacious cabin is viewable from above, surrounded by vibrant autumn foliage. A large wooden deck features patio furniture, including a red umbrella and seating area. Decorative stone walls and gravel pathways enhance the natural setting, with a tree-lined road curving nearby.
Cabin in Killington

Killington Golf&Mtn Biking. Hot tub & Fireplace!

LocationFamilyHiking

4.79 out of 5 average rating, 28 reviewsA blue house is framed by vibrant green foliage and blooming purple flowers in the foreground. The house features a front porch and is set against a backdrop of trees and a clear sky, providing a serene outdoor setting.
Cabin in Rutland

Blue Cozy Ski House

FamilyValueAmenities

4.76 out of 5 average rating, 59 reviews
Cabin in Chittenden

The music Cabin in Vermont, you will have fun

Destinations to explore