Find Vacation Rentals in Wintergreen Resort

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Popular Wintergreen Resort Vacation Rentals

Find the perfect Wintergreen Resort vacation rental

House Wintergreen Resort
from $345 per night
12 guests ∙ 5 bedrooms

House

5.0
Outstanding(24 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $278 per night
House ∙ 8 guests ∙ 4 bedrooms

130 m² House

4.9
Outstanding(132 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $431 per night
14 guests ∙ 6 bedrooms

House

4.9
Outstanding(41 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $456 per night
House ∙ 12 guests ∙ 6 bedrooms

228 m² House

4.8
Outstanding(47 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $535 per night
12 guests ∙ 5 bedrooms

House

5.0
Outstanding(94 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $356 per night
House ∙ 12 guests ∙ 5 bedrooms

265 m² House

5.0
Outstanding(319 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $159 per night
12 guests ∙ 3 bedrooms

House

4.8
Outstanding(16 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
Condo Wintergreen Resort
from $540 per night
Condo ∙ 15 guests ∙ 5 bedrooms

134 m² Condo

5.0
Outstanding(11 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
House Wintergreen Resort
from $641 per night
House ∙ 18 guests ∙ 5 bedrooms

390 m² House

4.9
Outstanding(60 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Vrbo
Details
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Vacation rentals with Wi-Fi

Condo  Wintergreen Resort
from $195 per night
Condo ∙ 8 guests ∙ 2 bedrooms

93 m² Condo

5.0
Outstanding(186 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
Vrbo
Details
Chalet  Wintergreen Resort
from $137 per night
Chalet ∙ 6 guests ∙ 3 bedrooms

105 m² Chalet

4.9
Outstanding(44 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
Vrbo
Details
Condo  Wintergreen Resort
from $540 per night
Condo ∙ 15 guests ∙ 5 bedrooms

134 m² Condo

5.0
Outstanding(11 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Internet
Vrbo
Details
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Cabins and Homes With Fireplaces

House  Wintergreen Resort
from $252 per night
House ∙ 14 guests ∙ 4 bedrooms

139 m² House

4.5
Excellent(2 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
HomeToGo
Details
House  Wintergreen Resort
from $435 per night
House ∙ 10 guests ∙ 7 bedrooms

307 m² House

5.0
Outstanding(153 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
Vrbo
Details
House  Wintergreen Resort
from $200 per night
House ∙ 6 guests ∙ 3 bedrooms

102 m² House

4.8
Outstanding(117 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Fireplace
Vrbo
Details
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Vacation Homes With Terraces

House  Wintergreen Resort
from $546 per night
House ∙ 12 guests ∙ 8 bedrooms

240 m² House

4.7
Excellent(83 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
Vrbo
Details
House  Wintergreen Resort
from $352 per night
House ∙ 6 guests ∙ 3 bedrooms

121 m² House

4.8
Outstanding(350 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
Vrbo
Details
House  Wintergreen Resort
from $231 per night
House ∙ 9 guests ∙ 4 bedrooms

174 m² House

4.7
Excellent(88 ratings)
Wintergreen Resort, Rockfish, Virginia, United States
Balcony/Patio
Vrbo
Details
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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 $139 per night.

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

On tripping.com, you will find 1,150 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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