25 Wintergreen Holiday Rentals

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Compare Wintergreen holiday rentals from 5 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

Looking for a vacation rental in Wintergreen? Tripping.com has 300 rental homes available in Wintergreen. Potential renters will find 2 studios, 30 1-bedroom, 94 2-bedroom and 174 rentals with 3 or more bedrooms ranging from $40 a night to $1950 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Wintergreen is $243 while the average price of a weekly rental is $1925. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Wintergreen home is $8250.

Wondering if you can bring your favorite dog or cat with you? We have 112 pet friendly vacation rentals available for you. In addition to accommodating pets, Wintergreen rentals offer a variety of amenities. In particular, 259 rentals have internet and wifi, 282 have TV and/or cable and 191 have a pool or hot tub.

Search properties from 5 rental sites in Wintergreen where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 253 HomeAway rentals, 42 TripAdvisor short term rentals and 3 Booking.com vacation rentals.