Chalet holiday rentals in Orleans County

4.96 out of 5 average rating, 97 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.

4.95 out of 5 average rating, 113 reviews

Chalet in Montgomery

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).

4.74 out of 5 average rating, 293 reviews

Peak & Quiet - Pet Friendly w/ Discount Lift Tix

This private house is four miles from Jay Peak Resort, boasting forest views and a brook running along the lower yard. This well-loved chalet has proudly provided a respite for mountain enthusiasts since 1969, with the last four decades under our family's care and the last eleven years as an Airbnb. Residing in the forest community of Alpine Haven, enjoy access to an eight-acre park, including scenic mountain views, nature trails, a summer pool, disc golf, sand volleyball, and more.

4.92 out of 5 average rating, 132 reviews

Chalet in Craftsbury

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.

4.91 out of 5 average rating, 86 reviews

The Shangri-la House

The Shangri-la House is an amazing 3 bedroom, 2 full bathroom chalet located in the Alpine Haven resort community in Northern Vermont. Guests of the house have access to the community pool, tennis court, volley ball court and hiking trails. The chalet is fully furnished, has high speed wi-fi, is dog friendly and is just 5 miles from The Jay Peak Ski, Golf and Indoor Water Park Resort. The chalet is also close to many restaurants the closest of which is .5 miles down the road.

4.92 out of 5 average rating, 98 reviews

Chalet in Jay

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!

4.92 out of 5 average rating, 132 reviews

Chalet in Troy

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

4.89 out of 5 average rating, 61 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!

Superhost

Chalet in Newark

4.91 out of 5 average rating, 32 reviews

Cozy Chalet w/ Hot Tub, Trails & Lake Willoughby

Escape to our charming Vermont ski chalet in the Northeast Kingdom. Enjoy 11 private acres with stunning mountain views. Relax in the hot tub, play in the game room, or explore private trails. Cozy up by the fireplace. Perfect for hiking, skiing, snowmobiling, and mountain biking near Kingdom Trails. End your day at the outdoor fire pit under the stars. Book now for the perfect blend of adventure and tranquility. Your Vermont escape awaits!

4.96 out of 5 average rating, 271 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.

4.98 out of 5 average rating, 99 reviews

Chalet in Newport

*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!!