Vacation rentals in Sugarloaf Mountain

Private Suite in the Green Mountains

Relax in a country setting, centrally located to Vermont attractions. This private apartment in the trees boasts three beds and a full kitchen. With views of the Green Mountains, you will be a short drive away from quaint towns, skiing, breweries, hiking, and swimming. On the property, enjoy the fresh mountain air, changing leaves, and local flora and fauna. In summer, cool off after a hike or bike in the shared pool. In winter, you're 15 minutes to Mad River Glen and 30 to Sugarbush Ski Resort.

Mountainside condo at Sugarbush!

Sugarbush at your doorstep! Ski, walk, hike, or bike from this cozy 1-br slope-side condominium steps from all resort amenities. Enjoy multiple dining options and mountain activities without getting in your car. Located on the first floor of the Center Village Condominium building, this unit offers ground-level access and designated parking. Enjoy the Mad River Valley with a short drive to Warren Village and Waitsfield for shops, dining, breweries and more. Please read all listing details.

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Quiet Alpine Suite for ski trips and lake days

This 1BR apartment in the quaint and quiet Alpine Village has a private deck, full kitchen, smart TV & pull-out sofa. Walk to Blueberry Lake & trails, then unwind by the fire pit or grill. Close to mountains, markets, bridges & byways—perfect for a foliage retreat or ski getaway (only 15 min to Sugarbush Resort). At Kismet Properties, we’re locals who can craft tailored tips & itineraries to enrich your trip—if you’d like. Please review rental agreement in House Rules before booking.

Cozy Cottage on the Clay Brook

Relax at this cozy, well-appointed cottage on the Clay Brook, where you can enjoy the sound of the river amidst a peaceful, wooded setting. Although it feels remote, we are conveniently located at Sugarbush Access Rd and Rte 100, making us easy to find! With all of Mad River Valley attractions nearby, the cottage is perfect for year-round enjoyment, whether you wish to cool off in the brook, roast marshmallows at the fire pit after hiking, admire the fall foliage, or unwind after skiing!

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Powder Days Retreat | Fireplace & Sugarbush Base

Looking for a place to truly disconnect? Welcome to your peaceful mountain escape in the heart of Mad River Valley. This 1BR condo offers the perfect balance of comfort and nature. Ideal for relaxing, skiing in winter or hiking, biking, fishing and exploring rivers and waterfalls in summer. End the day with mountain sunsets and quiet nights. A clean, warm space to reset with comfort and quiet. We created this space with love to welcome you. Come rest, venture, and feel at home.

Another Day in Paradise at Sugarbush Mountain

Steps to Sugarbush Mountain in Warren, Vermont. This a one bedroom, one bath condo located in Center Village on Sugarbush Mountain. Pull out sofa is also available in the main living room. Perfect for skiing, snow shoeing, mountain biking & hiking. Condo is walking distance to chairlift. Short drive to Warren Falls, Mad River Glen, Mount Ellen and many delicious restaurants. The condo is within walking distance (5 minutes) to Clay Brook Hotel, where many weddings are held.

Elegant 1-Bedroom Home in Stunning Location

Situated one mile from downtown Waitsfield, you can take it easy at this unique and tranquil getaway with stunning views of Sugarbush and Mad River Glen ski areas. Enjoy the outdoor patio with firepit, quiet/private setting, nearby amenities (skiing, biking, golf, fishing, ...), shopping in downtown Waitsfield and Warren Village, and nearby acclaimed eateries. Or, best of all, curl up with a good book and enjoy the peacefulness of this beautiful and unique home.

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

von Trapp Farmstead Little House

Come stay in the beautiful Mad River Valley! Our guest house named the Little House is surrounded by forest and 3.5 miles from the town of Waitsfield. Located on the North East corner of our farmland you'll find yourself less than a mile from our Farm Store where you can stock up on our organic cheeses, yogurts, and meats or beer, wine, and other provisions from over 40 local producers. Enjoy a quiet vacation or a skiing, hiking, biking, or rafting adventure!

Moonlight Farm Studio · Hot Tub · Vermont Retreat

Welcome, this is a Farmhouse. Unplug and recharge at Moonlight Mountain Farm, a peaceful Vermont farmstay surrounded by woods, fields, and mountain air. This private studio retreat is designed for couples or small groups seeking quiet, comfort, and a true rural escape — with an included indoor hot tub, mountain and pond views, and optional outdoor sauna. Whether you’re here to ski, hike, bike, or simply slow down, this is a place to reset.