Chalet holiday rentals in Orleans County

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).

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.

Peak & Quiet | Dog-Friendly w/ Pool, Park & Views

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.

Burke: Hot Tub, Kingdom Trails & Lake Willoughby

Escape to West Burke, VT. Hot tub, game room, trails, fire pit & mountain views. 🏔️ 11 secluded acres with breathtaking NEK mountain views ❄️ Minutes to Kingdom Trails, skiing, snowmobiling & biking ⛷️ Surrounded by top ski destinations- Burke Mountain , Jay Peak, and more 🍽️ Close to great local restaurants & bars 🔥 Cozy fireplace & outdoor fire pit under the stars 🛁 Relaxing hot tub with scenic views 🎯 Game room fun for all ages 🌲 Private trails for hiking & exploring

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.

Chalet Jay

Our cozy 3-bedroom, 2.5-bath chalet is just 7 minutes from Jay Peak Ski & Golf Resort. 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/snowshoe trails, Frisbee golf, playground, and park. With a backup generator and peaceful surroundings, it’s the perfect spot for relaxation or adventure. Book your stay today!

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.

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!

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.