Discover a selection of 408 vacation rentals in Wintergreen that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $60 per night, and houses and cabins are popular options for a stay in Wintergreen. Either way, you'll find a rental for everyone's needs.
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Destination guide

Alpine fun at Wintergreen vacation home rentals

An idyllic haven on the eastern slopes of the Blue Ridge Mountains, Wintergreen offers one-of-a-kind serenity and relaxation. Travelers are promised sweeping views of rippling streams, lush forests, and snow-tipped peaks from the doorstep of their Wintergreen vacation rental, but there’s more than just views on the itinerary. The 4-season Wintergreen Resort offers an unparalleled range of amenities to help you make the most of your peaceful retreat. You can chill out at the full-service spa, hit the links on one of 2 championship golf courses, or head for the great outdoors with winter snowboarding or summer hikes.

History

Heritage sites near Wintergreen vacation homes

Wintergreen is close to many fascinating historic sites and heritage museums to explore. Vacation rentals can be found near sights like Monticello, the presidential home of Thomas Jefferson, and Ash Lawn-Highland, the presidential home of James Monroe. You'll also like the Woodrow Wilson Presidential Library & Museum, the former president’s birthplace and museum with artifacts from his life.

Things to do

Tourist attractions near Wintergreen vacation rentals

The Rockfish Valley’s diverse ecosystem is proudly showcased at the Rockfish Valley Foundation Natural History Center, which is located within walking distance of most central Wintergreen vacation rentals. Open weekends between April and December, this center works to educate visitors on the historical and ecological features of the area. Their displays include a number of preserved native specimens, including black bears and wild turkeys, as well as collections of pelts, rocks, and other artifacts. Some of its most striking exhibits are on loan from the Virginia Museum of Natural History.

Activities

Things to do near Wintergreen vacation homes

The Wintergreen Resort is a major draw for winter sports enthusiasts, who flock here during the colder months to partake in snow tubing, skiing, and snowboarding. The Plunge is a 900 ft snow-tubing hill with 10 lanes and a 100 ft vertical drop. You can reach speeds of up to 40 mph as you whizz past some of the area’s most gorgeous scenery. Twenty-six slopes and 5 lifts making skiing another must in Wintergreen; the 129 acres of skiable terrain cater to all experience levels and 14 slopes are even lit up for night skiing, offering a new perspective on the landscape.

Day trips

Best excursions near Wintergreen vacation homes

Wintergreen is the ideal base camp to explore the sights of Charlottesville. Vacation homes are available near places like the Virginia Discovery Museum, a children’s museum with interactive exhibits on history and science, and the Rotunda, an iconic university building with notable architecture. You could also visit the Fralin Museum of Art at the University of Virginia, a large museum housing an extensive collection of artwork from different cultures and time periods, and McIntire Park, a city park with woods, streams, and recreational areas.

Weather

Climate during your stay in Wintergreen vacation homes

The resort’s popularity as a snow-sports destination means that Wintergreen vacation rentals are in high demand throughout the winter months. Temperatures are low, with averages falling to 34°F in January, while natural snowfall is bolstered by state-of-the-art snow-making machines. The mercury rises when summer rolls around, with July temperatures hovering around 75°F. Mountain breezes keep things cool, however, and artificial snow is in constant supply, so you'll still be able to hit the slopes. Due to this unique 4-season appeal, vacation rentals in Wintergreen are perennially in vogue.

Natural features

Blaze the Wintergreen trails

Part of the Virginia Birding and Wildlife Trail, the Rockfish River Loop Trail spans 6 miles and is a perfect spot for nature enthusiasts and bird-watchers to discover Virginia’s picturesque beauty. These trails also allow leashed dogs, so if you’re staying in a pet-friendly Wintergreen vacation rental, why not treat man’s best friend to a day out of their own? The Nelson Scenic Loop, meanwhile, is a 50-mile drive around Rockfish Valley that offers awe-inspiring views of the Blue Ridge Mountains, Crab Tree Falls, and the Appalachian Trail. Farmers markets, breweries, and wineries line the circular route, while spurs lead to hiking, biking, and birding trails.

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 center. 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 vacation rentals are available around Wintergreen?

Our 2020 property listings offer a large selection of 408 vacation rentals around Wintergreen. From 231 house rentals to 36 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Wintergreen:

  • Chestnut Springs: 163 vacation rentals
  • Pedlars Edge: 124 vacation rentals
  • Deer Springs: 159 vacation rentals
  • Treeloft: 153 vacation rentals
  • Laurel Ridge: 139 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Wintergreen?

Vrbo offers a large selection of vacation rentals near lovely places in Wintergreen. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Raven's Roost Overlook: 469 vacation rentals
  • Shenandoah Valley Art Center: 476 vacation rentals
  • Cardinal Point Vineyard and Winery: 582 vacation rentals
  • Walton's Mountain Museum: 470 vacation rentals
  • Blue Ridge Parkway North Entrance: 503 vacation rentals

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

Can I rent Houses in Wintergreen?

Yes, of course. Vrbo has 231 Houses in Wintergreen. Our other popular types of vacation rentals in Wintergreen include:

  • Cabins: 36 rentals available
  • Condos/Apartments: 155 rentals available
  • Cottages: 36 rentals available

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

Can I find a vacation rental with pool in Wintergreen?

Yes, you can select your preferred vacation rental with pool among our 236 vacation rentals with pool available in Wintergreen. Please use our search bar to access the selection of vacation rentals available.