Chalet vacation rentals in Orleans County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Orleans County

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Superhost

Chalet in Montgomery

4.86 out of 5 average rating, 21 reviews

Rustic Swiss Chalet - Minutes from JAY PEAK

Forget your worries in this spacious & secluded space as you step back in time in this Swiss style chalet. From the time you arrive you can nestle with family & friends in this 6 bedroom home with everything you need for a cozy stay. Make memories exploring local hiking trails just out the backdoor or hit up an Apres Ski after a day of skiing at local Jay Peak. The wood burning fireplace provides a warm oasis to play games or snuggle with a warm cup of your favorite beverage and a fuzzy blanket.

Guest favorite

Chalet in Westfield

4.98 out of 5 average rating, 53 reviews

Jay Peak Chalet in Alpine Haven

The house is meticulously clean & set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5 Bedrooms, 2.5 Bathrooms, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting 1/4 mi off Rte 242 with panoramic mountain views once leaves have fallen. Seasonal Pool, Disc Golf, Volleyball, Playground & Hiking Trails a short walk from the house. 3 mi to Jay Peak. Air Conditioning only in large upstairs bedroom (king bed) with desk.

Guest favorite

Chalet in Montgomery

4.94 out of 5 average rating, 101 reviews

Montgomery Meadows Chalet near Jay Peak

Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

Superhost

Chalet in Newark

4.86 out of 5 average rating, 14 reviews

Abbott Hill Chalet- Kingdom Trails/Hot Tub/Burke

Escape to this charming ski chalet nestled in Vermont's Northeast Kingdom. With 11 private acres, this hideaway boasts panoramic mountain views across its three levels. Relax in the hot tub, enjoy the basement's game room, explore the on-property trails or cozy up by the fireplace in the in the living room. Ideal for outdoor enthusiasts, it's a haven for hiking, skiing, snowmobiling, and mountain biking promising both relaxation and thrilling adventures amidst stunning natural landscapes.

Guest favorite

Chalet in Craftsbury

4.92 out of 5 average rating, 118 reviews

Vermont Log Home with Panoramic Mountain Views

A spacious light-filled log home in the heart of the Northeast Kingdom, with open kitchen, living room, sun room, wraparound deck, & basement ping-pong. Dazzling views of the Green Mountains and huge lawn for relaxation & play. Minutes from the 4-season Craftsbury Outdoor Center, Craftsbury General Store, Caspian Lake swimming, & the Hill Farmstead & Brewery. 50-minute drive to skiing & water park at Jay Peak, an hour to Stowe Mountain. Wood stove in the living room and free wifi.

Guest favorite

Chalet in Jay

4.92 out of 5 average rating, 66 reviews

Journeys End Chalet - Minutes to Jay Peak!

** BEAUTIFUL MOUNTAIN VIEWS** Welcome to the Journeys End Chalet! We are located just a quick 10 minute ride from the base of Jay Peak Resort, home to some of the best skiing and riding in the Northeast. The chalet is set on a beautiful and private 11 acres just a stones throw from the Canadian border. We love all dogs and your well behaved furry friends are welcome in our home. We are located directly on the VAST trail system so bring your snowmobile and enjoy!

Guest favorite

Chalet in Troy

4.91 out of 5 average rating, 102 reviews

Hidden Chalet 8 minutes from Jay Peak

This one of a kind property, formerly a Historic Grist mill (with ruins still on the property to explore) is surrounded on 3 sides by the Jay Branch River, a crystal clear mountain stream that runs down from Jay peak. The property is filled with Cedar and Maple and the sound of the River permeates through the trees. With multiple swimming holes and a 20 foot waterfall just steps from the deck there’s not another Airbnb like this in the state of Vermont.

Superhost

Chalet in Westfield

4.84 out of 5 average rating, 45 reviews

Greenshades, gorgeous chalet retreat @Jay Peak!

Welcome to Greenshades, a gorgeous swiss chalet hidden in the beautiful Northeast Kingdom, in the foothills of Jay Peak. Whether for a weekend away with your family, or more prolonged stays for those looking to work from home in the gorgeous north woods, Greenshades makes for a wonderful retreat. You can enjoy the great hiking, biking, food, waterfalls, road biking, mountain biking found locally from the peace and comfort of our alpine chalet!

Guest favorite

Chalet in Westfield

4.95 out of 5 average rating, 244 reviews

Mountain View Chalet near Jay Peak!

Welcome to your mountain getaway! Come unwind at this recently renovated chalet. The main living area and kitchen are perfect for all types of groups; couples, families and adventurers, and your pets! There are 13 acres to play (snowshoe, cross country ski, sledding, hiking or just relaxing) and only 20 minutes to awesome skiing or riding at Jay Peak! The views/sunsets from the property are breathtaking. 3 bedrooms, 2 baths across 2 floors.

Guest favorite

Chalet in Westfield

4.96 out of 5 average rating, 47 reviews

Enchanted Mountain Chalet Retreat near Jay Peak

**Welcome to Our Enchanting Chalet Retreat!** Experience the ultimate winter getaway at our charming 3-bedroom chalet, nestled near the slopes of the renowned Jay Peak Resort. Boasting a perfect blend of comfort and convenience, our cozy retreat is an ideal home base for your ski adventures. Step into a world of warmth, relaxation, and festive joy as you make unforgettable memories with your loved ones.

Guest favorite

Chalet in Newport

4.97 out of 5 average rating, 72 reviews

*Cozy Chalet on Memphremagog -Lake Views!

Welcome to our cozy chalet! This is a quiet and peaceful slice of paradise just steps from Lake Memphremagog. A great spot for a couple, friends or a family to sneak away to and enjoy outdoor recreation during any season! You’ll be very close to all the trails great for hiking, biking, snowmobiling, and cross country skiing. Less than 10 minutes to town and all amenities! Only 25 minutes to Jay Peak!!

Guest favorite

Chalet in Westfield

5.0 out of 5 average rating, 15 reviews

Edelweiss!: 5 Bed Ski/Summer Chalet near Jay Peak!

Welcome to Edelweiss our charming mountain ski chalet near Jay Peak Resort, Vermont! Nestled in the heart of the picturesque mountain landscape, this spacious and luxurious retreat is the perfect destination for your next family vacation or group getaway. Perfectly situated between Jay Peak Resort and Montgomery Center, enjoy all that this area has to offer.