Wintergreen Vacation Rentals, Nellysford: house rentals & more

Select from 53 houses, 163 condos, and other vacation rentals to find the perfect place for your stay in Wintergreen. Vacation homes offer the amenities you expect for your family, friends, or furry companion, such as a garden and pool. At the end of the day, you're sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Find the best place to stay - Wintergreen

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.

Sleeps 10 · 4 bedrooms · 2 bathrooms

Top rated rentals - Wintergreen

Main living floor contains dining, kitchen, living room, and half bath.

Premier Host

Quiet Getaway

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Why people love visiting beautiful Wintergreen

Enjoy the wineries and other features of Wintergreen. Travelers to this scenic city praise the mountain views, skiing and hiking. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Wintergreen

Do you want to discover attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Wintergreen has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Stoney Creek Golf Course (1.3 mi / 2.1 km)
Wintergreen Resort (3.2 mi / 5.1 km)
Afton Mountain Vineyards (8.9 mi / 14.3 km)
Veritas Vineyard and Winery (9.5 mi / 15.4 km)
Pippin Hill Farm & Vineyards (14 mi / 22.6 km)
King Family Vineyards (15.4 mi / 24.7 km)

Exploring the natural landscape of Wintergreen

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Wintergreen is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Crabtree Falls (10.1 mi / 16.3 km)
Blue Ridge Parkway North Entrance (10.3 mi / 16.6 km)
Rockfish Gap Entrance Shenandoah (10.8 mi / 17.4 km)
Reids Gap Trailhead (4.8 mi / 7.8 km)
Humpback Rocks (5.3 mi / 8.5 km)
Sherando Lake Recreation Area (6.8 mi / 10.9 km)

Seasonal weather averages in Wintergreen

Travelers enjoy Wintergreen for its skiing. If you've planned your trip around snowy activities, consider visiting in January, December, February or March, when snowfall averages 1 inches and temperatures average 38°F.

Traveling to and around Wintergreen

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 26.2 mi (42.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Charlottesville-Albemarle Airport (CHO), which is 30.3 mi (48.8 km) away.