Chalet vacation rentals in Orleans County

4.75 out of 5 average rating, 332 reviews

Peak & Quiet | Dog-Friendly 4 Miles from Jay Peak

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, Bucket Golf, and more.

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The living room features tall windows that provide ample natural light and overlook the surrounding wooded area. A stone fireplace is flanked by a television and cozy seating options, including a leather sofa and lounge chairs. A patterned rug adds texture to the wooden floor.

4.97 out of 5 average rating, 144 reviews

Cozy Chalet at Jay Peak

The house is set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5br, 2.5 Bath, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting 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 is in three bedrooms which are installed by the 2nd Sunday of June then removed the last Sunday of Sep.

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4.93 out of 5 average rating, 139 reviews

A green two-story house is viewed from a snow-covered path leading to its entrance. Thick layers of snow blanket the yard, while tall trees stand in the background against a clear sky, indicating a serene winter setting.

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).

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A three-story chalet is illuminated at night, showcasing warm light spilling from large windows. Snow blankets the ground, and an inviting front porch is adorned with railings. Pine trees surround the property, creating a cozy and serene winter atmosphere.

4.9 out of 5 average rating, 30 reviews

Chalet Jay | 7 Min to Jay Peak | Sleeps 8

Escape to our cozy 3-bedroom, 2.5-bath chalet just 7 minutes from Jay Peak Resort and Waterpark. Enjoy a fully stocked kitchen, gas fireplace, Bluetooth stereo, smart TVs, premium mattresses, luxurious linens, and large picture windows. Outdoor amenities include a gas grill, seasonal pool, tennis courts, hiking and snowshoe trails, frisbee golf, playground, and park. Set in a peaceful setting with a backup generator for added peace of mind, it’s the perfect spot for relaxation or adventure.

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4.9 out of 5 average rating, 50 reviews

The chalet exterior features a sloped green roof and a large deck extending from the front. Surrounded by trees, the brown structure harmonizes with the landscape under a clear blue sky, showcasing its welcoming presence in nature.

Chalet in Montgomery

Chalet Near Jay Peak Waterpark, Hiking & Skiing

Choose your season, choose your experience! Imagine arriving minutes from Jay Peak and instantly unwinding in our spacious 6-bedroom Swiss chalet, your cozy home base no matter the season. In the spring & summer step out the back door and discover breathtaking hiking trails, challenge yourself on Jay Peak's renowned golf course, or effortlessly celebrate with your wedding guests and friends at nearby Crofter's Green. Your home away from home, where there is something for every adventure!

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4.93 out of 5 average rating, 151 reviews

A spacious wooden deck extends outward, featuring a clear view of a green lawn and rolling fields. The surface displays a sunlit pattern of shadows created by the railing. In the background, gentle hills are visible under a cloudy sky.

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.

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The chalet is framed by lush greenery, showcasing a large deck and unique architecture. A fire pit is positioned in the foreground, surrounded by rocks, while two drinks are placed on a log, inviting guests to relax in the natural setting.

4.91 out of 5 average rating, 99 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.

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4.93 out of 5 average rating, 132 reviews

An aerial view showcases the chalet surrounded by lush greenery and a scenic landscape. The expansive wrap-around deck is visible, complete with outdoor seating and a fire pit. The property offers a gravel driveway and a separate storage shed, enhancing the overall outdoor space.

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!

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4.93 out of 5 average rating, 163 reviews

The exterior of the home is framed by vibrant autumn foliage, with a mix of yellow, orange, and green leaves. The house is set amidst tall trees, featuring a rustic wooden facade. A gentle slope leads to a pathway of stone steps, with a carpet of fallen leaves underfoot.

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.

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The living room features a vaulted ceiling with large windows, allowing natural light and scenic views of the outdoors. Cozy seating is arranged around a wooden coffee table, with a television on a wheeled stand. Decorative elements include a chandelier and an accent mirror.

4.89 out of 5 average rating, 64 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!

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The living area features high ceilings with exposed beams, allowing natural light to fill the space. A comfortable sofa is paired with accent chairs and a wood coffee table. A gas fireplace adds warmth, while a wall-mounted TV enhances entertainment options.

4.96 out of 5 average rating, 295 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.

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