Chalet holiday rentals in Addison County

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.

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

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!

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.

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!

Kismet Cabin: quiet, spacious, custom (sleeps 8)

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

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.

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.

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.