Ski-in/Ski-out vacation rentals in Wintergreen

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Brown Bear Lodge, walk to the slopes!

Welcome to The Brown Bear Lodge located at Wintergreen Resort nestled in the Blue Ridge Mountains. Enjoy this completely renovated 3 bed 2.5 bath house within walking distance to the main Wintergreen resort areas. All finishes and furnishings were thoughtfully curated to ensure a comfortable and relaxing stay. The main living area and bunk room are equipped with smart TVs logged into streaming services including YoutubeTV. We hope you enjoy your stay at our mountain getaway as much as we do!

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

Nestled in the heart of Wintergreen, This charming slope side 2-bedroom/ 2-bath. (sleeps six) condo steps from the slopes, offers a cozy retreat for your next vacation. As you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, microwave, and all the essential appliances and utensils you need to whip up delicious meals. Unwind in the living room by the crackling fireplace (wood provided for free), or enjoy a movie night on the smart TV.

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

All season 3bd/3ba ski out/in - Location & Views!

Spend your days hiking the area’s 30+ miles of trails, completing the ninja warrior course, soaring down a zip line at ~40mph, tubing down a hill longer than 3 football fields, playing volleyball/kayaking in the lake or ski out/ski in the patio door to the best ski area in the region! Bring your friends/family to enjoy special home away from home! Book today & enjoy our two-level, two fireplaces, 3 bathroom unit with a warm cup of coffee/tea experiencing top-rated views! Dog friendly!

Cozy Comfort with a View - Wintergreen Resort

Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.

Mtn/Firework Views from Private Deck ~ King Suite

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

Fantastic home in an ideal location, dogs welcome!

Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, 2br/2ba townhome, located in the heart of all the action. Ski check-in, Mountain Inn, restaurants, & the Market stocked with all the essentials located right next to our community. Come hike, swim in our private pool or lakes, ski, snowboard, tube, and vineyard, brewery, distillery, or cider hop. We have it all!