Chalet vacation rentals in Wintergreen Resort

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

2 min toSki! DogsOK Wood Stove Grill Fire Pit Hike

2min drive to skiing at Wintergreen Resort. Plucked from a German fairytale, this thoughtfully-designed oasis features intricate wainscoting and slate floors. Senses will be amazed with the attention to detail at each turn as you warm yourself at a wood-burning fireplace, a focal point of our living room, or have a fireside chat at the outdoor fire pit. Family and dog-friendly. Sleeps 8: Q, full, 2x twin, Q sofa bed, pack 'n play Fire pit Happy dog $187. Outdoor pool/tennis access in season

Opulent Retreat- Hot Tub* Fire Pit*Wheelchair Ramp

Immerse in the allure of mountain vistas at our luxurious retreat "Whiskey Ridge", nestled in the Wintergreen Resort. Savour the year-round adventures of skiing, hiking, golfing or exploring local wineries & craft beer hubs, just around the corner. A haven for up to 16 guests, our delightful home, complete with a carriage house, offers a comforting stay. Immense relaxation awaits families, friends or small corporate retreats in our fully equipped retreat, a perfect base to unwind this spring!

2 min toSki Hot Tub EV Charger Mountain View DogOK

2min drive to ski Wintergreen. Modern mountain vibe in this 4-season chalet nestled in the treetops. Hot tub, chef's kitchen and two spacious living rooms. This home invites indoor-outdoor living with a large deck with seasonal mountain view. Walking distance to trails, slopes, and restaurants. Sleeps 12: Q, Q, Q + bunk: 2x single + trundle, bunk: 2x single EV Charger Treetop, seasonal mountain views Fireplace Large deck w/ gas grill 3 Roku TVs Dog fee $187. Seasonal pools/tennis access.

Mountain Views, Hiking, Ski-Out @ Tyro

Welcome to Tequila Sunrise! Located slope-side at Tequila and Lower Tyro, our home offers a true ski-in/ski-out experience—step outside and you're on the slopes! Inside, you'll find an open floor plan featuring a fully stocked kitchen, a cozy family room that seats eight, and a huge wall of windows to watch stunning sunrises and skiers. In warmer months, enjoy the double-level deck, perfect for relaxing with family and friends amidst beautiful views. Your unforgettable getaway awaits!

Sleepy Bear Chalet

Escape to the mountains and enjoy your peace and quiet from the chaos of everyday life. Relax by the fire at night and sip your coffee in the morning while gazing out at the mountains. Our cozy home is only a 4 minute walk to Wintergreen Ski Resort where you can skii all day & then come back at night to stay in our 3 bedroom cozy chalet. Our stay is not only convenient to the ski resort but also hiking trails, Mountain Inn, special events, restaurants, bar, and convenience store.

5 beds/3 BR/2 BA, Chipmunk Chase at Wintergreen

Enjoy this 3 bed/2 bath home in Wintergreen all year round! Spring & Summer are great for hiking the Appalachian Trail, or visiting pools, nearby lakes & waterfalls. Fall brings beautiful colors along the Blue Ridge Parkway (2 miles) & Skyline Drive/Shenadoah NP (12 miles). Less than 1/2 mile to the WG Ski Slopes! There are many breweries, vineyards, cideries & even some distilleries nearby. Karaoke, Pac-Man, games, books & a gas fire table on the deck available for those cozy nights.

Luxury Chalet, Best Views in Virginia

Welcome to Blackrock Manor, a one-of-a-kind luxury chalet in Wintergreen that sleeps 16. Experience spectacular mountain views from all levels. Watch the sunset over the mountains from our signature “Eagles Nest.” Indulge in the indoor spa, then relax in the hot tub. With 2 living rooms, 6 bedrooms (4 masters), and a game room, there is plenty of space for groups. Managed by Chris R at New School Hosting- click on his profile below under "cohost" to see reviews for other properties.

Chalet house next to wineries/breweries!

Barn style chalet in the center of all the wineries, breweries, distilleries, cideries, Shen. National Park, hiking, App.Trail, Blue Ridge Pkwy, Wintergreen Resort. Pets welcome for an added fee ($40) per pet. Located on 151 -"alcohol alley". Literally seconds to Blue Mountain Brewery or Flying Fox Vineyard & a minute or two drive to Veritas, Cardinal Point, Afton Mt, Silverback, Valley Rd & so many more! Fiber internet, disinfected, whole foods delivers groceries here. Great spot!

410 Fawn Ridge Drive, Roseland Va 22967

This chalet offers a spacious panaromic view, with a high wooden vaulted ceiling. 1900 sq. ft. home. 1st floor master bedroom with king size bed and shower, double sink vanity, large jacuzzi-tub, half bath, and laundry room. Spacious living room with large walk out deck, propane BBQ grill, fire pit and tiki torches. Kitchen offers newer appliances, double sinks, dish washer, oven, microwave and duel drip style Carafe and Keurig coffee maker.

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Renovated 3BR/2.5BA mountain home is just a short walk to ski slopes, hiking trails, and resort amenities. Enjoy a private hot tub, stone fireplace, deck with views, gas fire pit, and grill. Kids will love the bunk room and loft with Buck Hunter arcade & games. Smart TVs with streaming in main living and bunk room. Fully stocked kitchen + washer/dryer. Perfect for ski trips, hiking getaways, winery weekends, or a relaxing mountain escape

Wintergreen Escape: Ski Slopes, Trails & Hot Tub

Wintergreen Ridge Retreat: Cozy Mountain Getaway Welcome to Wintergreen Ridge Retreat, your perfect escape at Wintergreen Resort, VA! Just 3 minutes from the ski slopes and snow tubing, our spacious and comfortable home offers a seamless blend of four seasons adventure. Whether you're carving down the slopes, exploring over 30 miles of hiking trails, or simply unwinding in the peaceful surroundings, this retreat has it all.