Chalet holiday rentals in Wintergreen Resort

Private Entrance Mountain Lodge Room/Nelson Rt151

Perfect for skiers & snowboarders! Private wing in Superhost’s home. Quiet, secluded lodge room with private bathroom and separate lockable guest entry. 2 queen beds. Light breakfast incl. Outdoor seating on elevated deck. Heated area to store outdoor gear. Separate glassed-in sitting room. Less than 2 mile to DB and Bold Rock. Minutes from App. Trail, Wintergreen, breweries, wineries, cideries, restaurants, hiking, outdoor festivals, & shopping. 1G WiFi, Smart TV. Complimentary coffee/tea/wine.

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

The River Cliff Lodge

Get away from the hustle of everyday life with this lovely mountain lodge. This cozy home is big enough for family gatherings or a group of friends to enjoy nature and the plentiful hiking trails that surround it. The area provides easy access to trails to hike (such as Crabtree Falls which is the tallest waterfalls on the east coast), fishing, seasonal skiing, biking routes, and plenty of wineries/breweries. Then relax in the home with a beautiful fireplace that is at the center of it all.

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.

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!

Secluded Mountain Cabin 12ppl + Trails & Firepit

Escape to a secluded mountain retreat in Lovingston, VA with 3BR + Loft, a spacious living area, and a private pool. Set beside 800 acres of hiking trails, this rustic yet comfortable home offers a Weber grill, fire pit, Sonos sound system, and fast WiFi. Relax by the pool, gather around the fire, or explore nearby wineries, breweries, and Charlottesville. Perfect for families, groups, and nature lovers seeking peace and adventure in the Blue Ridge.

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.

3 Masters Perfect for Multiple Families&NewArcade!

This is a true Post and Beam home in a spectacular natural setting. The home shows beautifully and is in great condition! Stunning views of the Blue Ridge Mountains. In a quiet but centrally located, distinguished neighborhood on the mountain at Wintergreen Resort. 4 min drive to the slopes. 5 miles to Skyline Drive. Three separate, very private bedrooms, each with their own full bath. You will fall in love with this true mountain home!!