Destination guide

Scenic Wintergreen will entice you

Enjoy the wineries and other features of Wintergreen. Travellers to this scenic city praise the mountain views, skiing and hiking. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Activities and attractions in Wintergreen

Do you want to discover attractions to see during your stay? Venture out of your cosy holiday rental and check out 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 centre:

  • Wintergreen Resort (1.7 mi / 2.8 km)
  • Stoney Creek Golf Course (1.9 mi / 3 km)
  • Hill Top Berry Farm & Winery (3.7 mi / 6 km)
  • Cardinal Point Vineyard and Winery (8.2 mi / 13.1 km)
  • DelFosse Vineyards and Winery (8.3 mi / 13.4 km)
  • Mountain Cove Vineyards (8.6 mi / 13.9 km)

Seasonal weather averages in Wintergreen

Travellers enjoy Wintergreen for its skiing. To make the most of the cold weather activities, you might consider visiting in January, December, March or July, when snowfall averages 3.13 inches and temperatures average -5°F.

Natural features

Exploring the natural landscape of Wintergreen

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Wintergreen is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Sherando Lake Recreation Area (5.2 mi / 8.4 km)
  • Blue Ridge Parkway North Entrance (9.5 mi / 15.3 km)
  • Rockfish Gap Entrance Shenandoah (9.9 mi / 16 km)
  • Viette's Gardens (15.7 mi / 25.3 km)
How to get there

How to get to and around Wintergreen

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 25.1 mi (40.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Charlottesville, VA (CHO-Charlottesville-Albemarle), which is 30.4 mi (49 km) away.

How many holiday rentals are available around Wintergreen?

Our 2020 accommodation listings offer a large selection of 415 holiday lettings around Wintergreen. From 186 houses to 32 cabins, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What is the best area to stay when travelling to Wintergreen?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Wintergreen:

  • Chestnut Springs: 161 holiday homes
  • Treeloft: 182 holiday homes
  • Pedlars Edge: 158 holiday homes
  • Laurel Ridge: 172 holiday homes
  • Deer Springs: 160 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Wintergreen? offers a large selection of holiday accommodations near great places in Wintergreen. From travellers, the most popular points of interest to stay near are:

  • Raven's Roost Overlook: 491 holiday lettings
  • Pippin Hill Farm & Vineyards: 644 holiday lettings
  • Staunton Station: 422 holiday lettings
  • Swannanoa Palace: 515 holiday lettings
  • Hermitage Hill Farm & Stables: 521 holiday lettings

But there are many other points of interest around Wintergreen listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Wintergreen?

Yes, of course. offers 186 Houses in Wintergreen. Our other popular types of Wintergreen holiday rentals include:

  • Cabins: 32 self catering accommodations
  • Flats: 155 self catering accommodations
  • Cottages: 32 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.

Can I find a holiday accommodation with pool in Wintergreen?

Yes, you can select your preferred holiday accommodation with pool among our 286 holiday homes with pool available in Wintergreen. Please use our search bar to access the selection of holiday rentals available.