Photo by Rebecca Brent
Wintergreen vacation rentals
We found 831 vacation rentals — enter your dates for availability
Select from 52 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 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
Find spaces that suit your style
House
Condo/Apartment
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
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.