27 Wintergreen Holiday Rentals

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Compare Wintergreen holiday rentals from 4 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $40 to $1950 a night.
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Information about Wintergreen

About Wintergreen

With 30 miles of biking and hiking trails, Wintergreen is a small town in Virginia that is mostly made up of Wintergreen Resort—a four-season mountain retreat located in the Blue Ridge Mountains’ eastern slopes, which has been named “Best Ski Resort” by multiple media outlets. There is also an abundance of outdoor activities that visitors come to enjoy, among them skiing, golfing, biking, hiking and mountain climbing. Wintergreen is a great place to come and enjoy the outdoors while escaping the hustle and bustle of everyday life.

Things to Do in Wintergreen

The River Bluff House, which is said to be the oldest standing structure in the area, was built in 1805 and stands along the south fork of the Rockfish River. Since 1980, it has been listed on the National Register of Historic Places and serves as a great example of Palladian-style architecture. Skiing is the most popular activity at Wintergreen Resort, although people also come to go hiking, horseback riding, snowboarding, hunting and fishing. The resort is also home to world-class golf and tennis facilities for those who want to participate. Recommended golf courses include Devils Knob on the mountain, and Stoney Creek in the valley—private and group lessons are available. Despite its smaller size, Wintergreen has a variety of restaurants, offering visitors multiple dining options when they visit—ranging from French cuisine to classic American. Bold Rock features a cidery and tap room and is a great place to get a drink, and some of the other restaurants even offer live music on weekends. The resort also has a world-class spa, which offers indoor and outdoor pools, exercise equipment and relaxing treatments to nurture the body. The resort’s Discovery Ridge Adventure Center also offers fun for the whole family, including miniature golf, rock climbing, and even a skate park.

Day Trips Near Wintergreen

The city of Charlottesville is just 40 minutes away from Wintergreen and is home to Shenandoah National Park, as well as Monticello—Thomas Jefferson’s famed plantation home. Richmond, the capital of Virginia, is one of the oldest cities in America and is just over an hour and a half way from Wintergreen. Other great day trips near Wintergreen include Roanoke (less than two hours), Lynchburg (under an hour), and Virginia Beach (three hours).

Wintergreen Accommodation

A majority of the homes for sale in Wintergreen are single-family style, although there are some condos located within the resort as well. Apartments and attached homes are of the rare variety in this particular region. Most of the homes in the area offer stunning views of the woods and golf courses, and provide access to nature trails. Properties tend to be quite spacious with large decks, yards and garages for multiple vehicles.

Transportation in Wintergreen

Transportation is limited in Wintergreen; there is no nearby bus or rail system, which is why renting a car is the primary way to get around town. There is a ski shuttle available at the resort. Taxis are not readily available either, but the town is pedestrian-friendly and has lots of great trails for cyclists and hikers.

Vacation Rentals in Wintergreen

Find the best Wintergreen vacation rentals with Tripping.com. Choose from 313 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $40 a night to $1950 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 254 of homes in Wintergreen offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 188 rentals with pool or jacuzzi, or relax with the family in one of the 285 homes with cable TV.

For all those dog lovers and cat lovers, Wintergreen offers 111 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 4 rental sites in Wintergreen where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 255 HomeAway rentals, 40 TripAdvisor short term rentals and 17 Booking.com vacation rentals.