Chalet vacation rentals in Orleans County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Orleans County

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Guest favorite

Chalet in Westfield

4.96 out of 5 average rating, 82 reviews

Cozy Chalet at Jay Peak

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, 103 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).

Guest favorite

Chalet in Morgan

4.91 out of 5 average rating, 11 reviews

Peaceful Lake House in the Northeast Kingdom

Get away from it all at this charming home on Lake Seymour, renown for its crystal-clear water and Northeast Kingdom serenity. With its private beach and dock, your family can enjoy swimming, boating, and fishing in the Summer or relaxing in the gorgeous vistas from the spacious stone patio with its brand new hot tub. Come for Vermont's famous Fall foliage, or the nearby access to snowmobile/ATV trails in the VAST system in Winter, with proximity to two ski areas less than an hour away.

Guest favorite

Chalet in Montgomery

5 out of 5 average rating, 10 reviews

The Chalet Getaway, 3 Baths, 5 Bedrooms, 12 Beds

Relax with the family or friends at our peaceful Chalet Getaway. Located just 4 miles from Jay Peak Ski Resort & Golf Course. Enjoy our beautiful well maintained Vacation home that has 5 bedrooms, 3 baths and a large open social area. There is a separate game room with TV & foosball for the kids. In the summer there is a pool, disc golf course, a park and a tennis/pickle ball court in our plan for your use. The Jay Peak/Montgomery Center, area has incredible restaurants & something for All.

Guest favorite

Chalet in Burke

4.98 out of 5 average rating, 43 reviews

Cozy Chalet/Ski, Bike, Hike

This is it... your Vermont Vacation Getaway where you can experience all that the Northeast Kingdom offers. Tranquility, privacy, yet located in the middle of your next adventure. Trailside convenience to Mountain Biking right out the front door - easy access to Kingdom Trails via connecting Swamp Donkey Trail... close to Burke Mountain skiing/snowboarding and VAST trail... snowshoeing, hiking, fishing... or relax on the deck overlooking the pond, and enjoy the view of Burke Mountain.

Guest favorite

Chalet in Craftsbury

4.92 out of 5 average rating, 124 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.

Superhost

Chalet in Newark

4.88 out of 5 average rating, 25 reviews

Burke Chalet- Skiing/VAST Trails/Hot Tub

Escape to this charming ski chalet in Vermont's Northeast Kingdom. With 11 private acres, this hideaway offers panoramic mountain and foliage views. Relax in the hot tub, enjoy the game room, explore the trails, or cozy up by the fireplace. Ideal for outdoor enthusiasts, it’s perfect for hiking, skiing, snowmobiling, and mountain biking, with Vermont's Kingdom Trails nearby. Unwind at the outdoor fire pit, promising relaxation and thrilling adventures amidst stunning landscapes.

Guest favorite

Chalet in Jay

4.92 out of 5 average rating, 91 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

4.92 out of 5 average rating, 114 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

4.92 out of 5 average rating, 50 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, 252 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 Newport

4.98 out of 5 average rating, 88 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!!