Chalet vacation rentals in Winhall

Family Chalet Huge Yard Near Bike Hike Swim Golf!

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

Value · Family · TV

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

Value · Family · Walkability

Haus Nowak - spacious family-friendly retreat

Our home is privately set on a dirt road less than 2 miles from town or a short drive to ski areas. Nestled in a wooded acre with wandering paths, it is perfect for those who want to be close to all Manchester offers yet quiet and comfortable for reading, music, or mid-day naps on the deck or screen porch. Go river walking or hike the Lye Brook Wilderness and AT trails? It’s less than a mile from the house- walk, bike, or drive to the trailheads. *Note: 6 adults (or less)+children is ideal !

Location · Family · Air conditioning

4BR Ski Chalet | Hot Tub | Mins to Stratton, VT

Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

Location · Value · Quiet

Shiny Elk Chalet - near Mt Snow w/ cozy fireplace

The Shiny Elk Chalet is your bright and sunny mountain home located in the Southern VT near the Green Mountain National Forest just 7 miles from Mount Snow Ski Resort, and 13 miles from Stratton Mountain. Rest and relax on a small private cul-de-sac. Huge windows and filled with natural light in the afternoon. Summer: enjoy the firepit and make some s'mores! Grill on our propane grill and enjoy the beautiful stone patio and patio furniture. Explore the local towns, waterfalls, and the VT.

Family · Location · Getting around

Mountain view chalet with hot tub & fire pit!

Welcome to the @vermontviewchalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Value · Family · Indoor spaces

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Family · Value · Decor

Brook House: Hot Tub, Fire Pit, Ping Pong, Mt Snow

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food southern VT has to offer!

Value · Location · Parking

Chalet 1mi to Mount Snow with theater and hot tub

✔ Freshly Renovated & Furnished In 2025 ✔ 1 Mile To Mount Snow, On The MOOver Route ✔ 7-Person Hot Tub Under String Lights ✔ Fire Pit w/ Adirondack Chairs ✔ Theater Room w/ Real Theater Seats ✔ Game Room with Air Hockey, Shuffleboard, Arcades, Bar, and SMART TV ✔ Air Conditioning ✔ Fast Fiber Optic Wifi ✔ Dog-Friendly (w/ fee) ✔ All linens, towels, and basic soaps are provided. ✔ We also provide one Pack N' Play and one High Chair ✔ Full-Size Washer & Dryer

Family · Location · Hot tub

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

Value · Location · Walkability

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

Value · Family · Air conditioning

Luxe HotTub, Sauna, Fall Leaves, Stratton /Mt Snow

Escape to HYGGE HOUSE VERMONT, your cozy and modern mountain getaway. Come relax and make memories with family and friends in a luxurious retreat on 4 wooded acres. Unwind in the private HOT TUB and SAUNA. Just minutes from both Stratton Mountain and Mount Snow, this architectural gem is the perfect blend of seclusion and adventure. Features high-speed internet, a gourmet kitchen, and a cozy stone fireplace.

Location · Value · Decor