Chalet vacation rentals in Addison County

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Top-rated chalet rentals in Addison County

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The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.
Chalet in Stockbridge
4.9 out of 5 average rating, 189 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

Guest favorite
An open living and dining area features a combination of wooden walls and ceiling beams. Large windows allow natural light to fill the space, providing views of the outdoor surroundings. A stone fireplace is situated against one wall, with comfortable seating arranged nearby.
Chalet in Waitsfield
4.79 out of 5 average rating, 91 reviews

The Mad House

Enjoy the beautiful Mad River Valley while staying at The Mad House – a classic Vermont ski chalet in Waitsfield, VT! Ideally located <4 miles from Sugarbush Resort + Mad River Glen, this spacious, charmingly retro, family-oriented house accommodates large groups for your ski vacation or weekend getaway. Easy access to hiking, cycling, golf, tennis, leaf peeping, swimming, and many local wedding venues, such as the nearby Inn at the Round Barn Farm, among others in the Waitsfield/Warren area.

Guest favorite
An aerial view captures the modern chalet nestled amidst vibrant autumn foliage. The surrounding landscape reveals rolling hills and expansive mountain views under a soft, cloudy sky, highlighting the property's secluded location.
Chalet in Stockbridge
4.93 out of 5 average rating, 45 reviews

Private Mountain Sanctuary | 15 Min to Killington

*Winter Stays* Must have 4WD vehicle with snow tires or snow chains. We want you to make it safely up the mountain for those breathtaking views! This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! Wow: - Designer modern chalet on 150+ private acres - Off-grid privacy, while 15 minutes to Killington. 5 min to world class mountain bike trails. - 360 degree panoramic view - VAST trail, walking trails - Hike, Bike, Ski, Snowshoe, Stargaze, Views Views Views!

Top guest favorite
A spacious living area is showcased, featuring a red sectional sofa positioned around a round coffee table. Natural wood beams cross the ceiling, complementing the stone fireplace. Two modern chairs are arranged nearby, with a decorative plant on a side table, enhancing the welcoming ambiance.
Chalet in Waitsfield
4.97 out of 5 average rating, 144 reviews

Warm Luxury Mid-Century Modern Chalet

Woodward Haus is a stylish MCM retreat with wood, glass, & stone design. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swimholes, farms, hiking, road & mtn bike, golf, climbing, tubes on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

Guest favorite
Floor-to-ceiling glass doors reveal expansive mountain views, allowing natural light to dominate the space. A comfortable chair is positioned nearby, inviting relaxation while enjoying the scenic landscape. The wooden floor adds warmth to the room, enhancing the serene atmosphere.
Chalet in Warren
4.78 out of 5 average rating, 59 reviews

Chalet In The Clouds: Your Pure Vermont Escape

This Scandinavian-inspired retreat sits high in the Green Mountains, offering stunning views of Sugarbush and Lincoln Gap. Enjoy unforgettable sunsets from the wrap-around balconies and unwind in the peaceful surroundings. Whether you’re skiing, hiking, or relaxing by the wood-burning stove or outdoor gardens and fire pit, this home is the perfect getaway for nature lovers seeking comfort, tranquility, and adventure, just minutes from world-class outdoor activities and mountain resorts.

Guest favorite
The snowy exterior of the ski house is illuminated by warm light emanating from the windows, creating a cozy ambiance. Wooden steps lead down to the entrance, framed by bare trees, enhancing the winter setting.
Chalet in Warren
5 out of 5 average rating, 29 reviews

The Snow'd Inn!

This bright 2 bedroom 1 1/2 bath ski house makes for a great multi season getaway. Brand new kitchen counter and full size laundry in '22. Bedrooms newly furnished, complete with desk for working remote. Lots of natural light to enjoy after an adventurous day in the mad river valley. We are ski in/ walk out snow dependent and minutes from Mt Ellen and Mad River. Mountain Biking, snowshoe and hiking trails at Sugarbush are steps away. A common pool and tennis courts during the summer.

Guest favorite
A comfortable living area is furnished with a light-colored sofa accented by two decorative pillows. Two dark ottomans are positioned in front of the sofa. Large windows frame a view of the surrounding greenery, with curtains that gently enhance the natural light.
Chalet in Warren
5 out of 5 average rating, 79 reviews

Inviting 2-bedroom chalet with views!

Welcome to this charming 2-bedroom, 1-bathroom mountainside chalet, nestled amidst breathtaking views of the Mad River Valley. Immerse yourself in modern comfort, featuring Moen fixtures and GE appliances that ensure a luxurious stay. Cozy up to the inviting gas fireplace, and you might find yourself reluctant to go outside. But fear not, as the Lincoln Peak base area is a stone’s throw away, offering easy access to all the amenities. This is the perfect retreat you’ve been dreaming of!

Guest favorite
Chalet in Warren
4.8 out of 5 average rating, 10 reviews

Handcrafted Log Chalet (sleeps 2-4)

Welcome to our Vermont cabin—a spacious, light-filled retreat built from locally harvested logs and surrounded by gardens and quiet. Inside: an open loft w/ queen bed, window seat, and built-in closets; full bath w/ shower; fully equipped kitchen; wrap-around couch w/ queen pullout; smart TV, A/C, washer/dryer. Outside, enjoy the fire pit, wrap around deck, back porch w/ Adirondack chairs, blooming gardens, woodland paths, and easy access to swimming holes, trails, and fall colors.

Top guest favorite
The entrance to the mountain cottage is showcased, featuring a black front door framed by wooden accents. Hanging planters with greenery are attached above the door, and a gravel pathway leads through a serene wooded area. Soft outdoor lighting is present along the path.
Chalet in Warren
4.99 out of 5 average rating, 77 reviews

Brand New Mountain Chalet

Just a few nights left for foliage season! Built in 2023 and located only a half mile from Historic Warren Village, this peaceful mountain cottage has 1 full bedroom and a gorgeous finished loft. Each private space has a king bed, it's own bathroom and new furniture. Inside, the bright and spacious interior boasts modern finishes, brand new appliances and a rustic country charm. Outside, relax in the serenity of the surrounding forest, and take in the view of Sugarbush Resort.

Guest favorite
The living area is characterized by a stone fireplace and wooden beams. A stylish striped sofa and a mid-century chair are positioned near a modern hanging chair. Large windows allow natural light to illuminate the space, while a coffee table completes the inviting atmosphere.
Chalet in Pittsfield
4.86 out of 5 average rating, 37 reviews

The Sklarzhaus

This spacious mountain chalet offers views of both Killington and Pico looking out over your 2 story deck. Decorated with original Scandinavian light fixtures, vintage ski posters & wood burning fireplace, it is a skiers' dream getaway. With an entertainer’s kitchen updated with modern appliances, a huge island, and expandable dining table - this house is perfect for groups and families to enjoy. Recently installed heat/ac system quietly keeps you comfortable summer and winter.

Top guest favorite
A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.
Chalet in Stockbridge
4.97 out of 5 average rating, 143 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Guest favorite
Chalet in Rochester
4.79 out of 5 average rating, 58 reviews

Vermont Dream Mountain Cabin.

Our beloved home is a cozy, fully equipped cabin nestled in Vermont’s Green Mountains National Forest. Secluded yet just 10 minutes from town and 25 from the nearest ski area, it features a warm interior and a spacious deck overlooking the forest—perfect for relaxing. Enjoy hiking, biking, snowshoeing, skiing, swimming in the community pond, or cooling off in nearby waterholes. A peaceful mountain escape surrounded by nature.

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