Chalet holiday rentals in Addison County

4.92 out of 5 average rating, 183 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

4.97 out of 5 average rating, 168 reviews

Chalet in Fayston

4BR Mad River Valley Chalet w/ View, Close to All

*Featured in Food + Wine Magazine!* Welcome to Stars Hollow Chalet, perfect for a romantic getaway, family and friend getaways, or remote work with super-fast internet (rare in the area!). We're on the Fayston/Waitsfield line fantastically close to downtown shops, food, swimming & skiing. Explore all the Mad River Valley has to offer right down the street, then retreat back to the chalet, switch into your slippers and cozy up on our comfy green velvet and leather couches by the fireplace.

4.8 out of 5 average rating, 86 reviews

Chalet in Waitsfield

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.

Top Guest favourite

4.94 out of 5 average rating, 48 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

BENT TREE has a spectacular view of the mountain valley and overlooks the scenic VT Rte 100. The chalet designed by a famous architect, gives you everything you want for a perfect getaway. Featuring 4 bedrooms and 3.5 bathrooms, with a tatami game room. 25 mins to Killington Ski Area, 20 mins to Mtn Meadows for XC Ski, and 45 mins to Sugarbush. Great for guests that want winter activities and nature views. Enjoy working remotely with FAST fiber and 3 different workplaces. @BentTreeVermont

Superhost

4.95 out of 5 average rating, 41 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!

4.96 out of 5 average rating, 141 reviews

Chalet in Waitsfield

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

Superhost

4.79 out of 5 average rating, 48 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.

Top Guest favourite

5 out of 5 average rating, 31 reviews

Handcrafted Log Chalet: quiet, spacious, custom

Just steps away from an array of adventures, wedding venues, & tranquil retreats, this custom log home is ideal for friends, families, and multigenerational gatherings. - 3 BR w/queen beds - short loft w/ 2 twin beds - 2 queen sofa beds - 2 living rooms - 2 fully stocked kitchens - 2 bathrooms - whirlpool bathtub w/ artisanal Lavender Salt Soak - wrap-around deck w/ grill - quaint backyard w/ fire pit - covered porch w/ porch swing - woodland garden - quiet friendly neighborhood

Top Guest favourite

4.98 out of 5 average rating, 65 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.

4.91 out of 5 average rating, 23 reviews

Chalet Vermont - Ski In/Ski Out at Sugarbush

This 1963 four-season remodeled ski Chalet is one of the original homes built right on the trails of Sugarbush. You will enjoy a historic yet modernly furnished and immaculately maintained home. Soak in views of the mountain beside the wood stove or boot-up in the mudroom and walk down the road to where you can access the trail. Ski home for lunch or to celebrate a great day in classic après style. Perfect for spring skiing, summer swimming/biking, and autumn leaf-peeping.