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Wintergreen Resort
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Popular Wintergreen Resort Vacation Rentals

Find the perfect Wintergreen Resort vacation rental

Cabin Wintergreen Resort
from $259 per night
Cabin ∙ 8 guests ∙ 3 bedrooms
4.6
Excellent (80 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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Villa Wintergreen Resort
from $492 per night
Villa ∙ 13 guests ∙ 6 bedrooms
4.3
Very good (47 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $336 per night
House ∙ 10 guests ∙ 4 bedrooms
4.8
Outstanding (135 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $101 per night
House ∙ 10 guests ∙ 3 bedrooms
4.9
Outstanding (88 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $440 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (19 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $286 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $409 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding (12 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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House Wintergreen Resort
from $568 per night
House ∙ 16 guests ∙ 5 bedrooms
5.0
Outstanding (20 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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Chalet Wintergreen Resort
from $134 per night
Chalet ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (34 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
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Cabins and Homes With Fireplaces

Cabin  Wintergreen Resort
from $309 per night
Cabin ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (89 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
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Condo  Wintergreen Resort
from $242 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding (26 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
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House  Wintergreen Resort
from $198 per night
House ∙ 14 guests ∙ 5 bedrooms
4.7
Excellent (53 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
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Vacation Homes With Terraces

House  Wintergreen Resort
from $144 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (12 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
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House  Wintergreen Resort
from $389 per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding (63 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
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House  Wintergreen Resort
from $642 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (146 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
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Vacation rentals with Wi-Fi

House  Wintergreen Resort
from $424 per night
House ∙ 18 guests ∙ 5 bedrooms
4.9
Outstanding (58 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
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House  Wintergreen Resort
from $340 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (308 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
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House  Wintergreen Resort
from $266 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (15 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
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Frequently Asked Questions

Can I find cheap vacation rentals in Wintergreen Resort?

You can book a vacation rental in Wintergreen Resort for as little as $93 per night.

Can I see all vacation rentals that are available in Wintergreen Resort?

On tripping.com, you will find 744 available vacation rental offers in Wintergreen Resort.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Wintergreen Information

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.

Popular Day Trips Near Wintergreen Resort

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