Chalet holiday rentals in Windsor County

Hillcrest Manor of Vermont

Perched like a crown upon a sweeping hill, where the earth rises in graceful, rolling waves to meet the heavens, Hillcrest Manor stands as one of the most desired and extraordinary vacation sanctuaries in all Vermont. This is not merely a home — it is a private kingdom of light, legacy, and breathtaking beauty. A place where important hearts have found refuge, where dawn paints the world in strokes of rose and gold, + where the ancient rhythms of forest and sky restore the spirit like no other.

Value · Family · Long stay

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

Value · Family · Layout

Slippery Slope Chalet | 5 min to Base & Nightlife

Slippery Slope Chalet sits in the heart of Killington, just 5 minutes to the K1 Base Lodge and 2 minutes to the Access Road's restaurants, bars, and shops. Our rustic 4-bedroom, 2-bath retreat sleeps up to 8, ideal for families and groups: The house boasts a fully stocked gourmet farmhouse kitchen, open-concept living area, A covered hot tub, spa-like baths with rain showers and heated floors, an arcade room, and a 4-season sunroom for both lounging and gear storage with a boot and glove dryer.

Location · Family · Skiing

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Location · Value · Parking

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Value · Location · Decor

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

Value · Location · Hot tub

Private Mountain Sanctuary | 15 Min to Killington

This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! *NO Air conditioning. Most summer nights are cool and breezy, and we do have an industrial sized fan, but no AC due to off-grid solar set up. Wow: * Designer modern chalet on 150+ private acres of Vermont wilderness * Off-grid privacy with hiking trails, stargazing, complete seclusion * World-class mountain biking 5 minutes away. 360-degree panoramic views * Hike, Bike, Explore, Stargaze, Views Views Views!

Value · Location · Bathroom

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Ledges Unit is a recently updated home away from home just 2 miles from Killington’s Skyship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. View sister listings by clicking my Host profile picture below. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom.

Value · Family · Quiet

Scandinavian design Chalet hiking trail + hot tub

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

Value · Family · Cleanliness

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.

Family · Value · Nearby

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.

Family · Value · Bathroom

Tranquil Brookside Retreat with Hot Tub & Firepit

Imagine waking to the gentle sound of a babbling brook, soaking in your private hot tub beneath a star-filled Vermont sky, and sharing s'mores and laughter around a crackling fire with the people you love most. This is the Brookside Retreat—a thoughtfully designed 4-bedroom home where memory-making moments happen naturally, whether you're gathering for a weekend escape, a family reunion, or a quiet retreat with friends.

Location · Family · Outdoor spaces