Wintergreen Vacation Rentals, Nellysford: house rentals & more

Select from 53 houses, 163 condos, and other vacation rentals to find the perfect place for your stay in Wintergreen. Vacation homes offer the amenities you expect for your family, friends, or furry companion, such as a garden and pool. At the end of the day, you're sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Find the best place to stay - Wintergreen

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.

Sleeps 10 · 4 bedrooms · 2 bathrooms

Find spaces that suit your style

Top rated rentals - Wintergreen

Good morning! Spectacular sunrise from the living room and deck!

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Why people love visiting beautiful Wintergreen

Enjoy the wineries and other features of Wintergreen. Travelers to this scenic city praise the mountain views, skiing and hiking. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Wintergreen

Do you want to discover attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Wintergreen has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Stoney Creek Golf Course (1.3 mi / 2.1 km)
Wintergreen Resort (3.2 mi / 5.1 km)
Afton Mountain Vineyards (8.9 mi / 14.3 km)
Veritas Vineyard and Winery (9.5 mi / 15.4 km)
Pippin Hill Farm & Vineyards (14 mi / 22.6 km)
King Family Vineyards (15.4 mi / 24.7 km)

Exploring the natural landscape of Wintergreen

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Wintergreen is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Crabtree Falls (10.1 mi / 16.3 km)
Blue Ridge Parkway North Entrance (10.3 mi / 16.6 km)
Rockfish Gap Entrance Shenandoah (10.8 mi / 17.4 km)
Reids Gap Trailhead (4.8 mi / 7.8 km)
Humpback Rocks (5.3 mi / 8.5 km)
Sherando Lake Recreation Area (6.8 mi / 10.9 km)

Seasonal weather averages in Wintergreen

Travelers enjoy Wintergreen for its skiing. If you've planned your trip around snowy activities, consider visiting in January, December, February or March, when snowfall averages 1 inches and temperatures average 38°F.

Traveling to and around Wintergreen

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 26.2 mi (42.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Charlottesville-Albemarle Airport (CHO), which is 30.3 mi (48.8 km) away.

Frequently asked questions

What is the best area to stay in Wintergreen when booking a vacation rental?

Pedlars Edge is one of the more desired locations to book a vacation home in Wintergreen. Settle in here and enjoy all the privacy and convenience that comes with having a place all to yourself.

What is the most popular type of vacation rental accommodation in Wintergreen?

Condos are the most popular type of vacation rental in Wintergreen, according to our data. Even if you've got a different vision in mind, Vrbo has vacation homes in a variety of shapes and sizes. Explore our options to find your ideal match.

How much does it cost to rent a vacation rental in Wintergreen?

Different factors affect how much you'll pay for a vacation rental in Wintergreen, like the time of year, property type and length of stay. However, all of our vacation homes have one thing in common — exceptional value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Wintergreen?

The average price for a vacation rental by the beach in Wintergreen depends on when you're traveling and the size and style of property you're looking for. Find prices easily on Vrbo by entering your travel dates. Then use the handy filters to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.

Are there pet-friendly vacation rentals in Wintergreen?

Pack a travel bag and a bone for the pup in your life because Wintergreen has 378 properties that open their doors to pets. Let your furriest pal enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.

Can I rent a house with a pool in Wintergreen?

Tick the "pool" box in our handy filter tool and choose from 236 houses with private pools in Wintergreen on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your Vrbo vacation home has its own swimming pool.

What are popular rental amenities in Wintergreen?

Some of the most popular rental amenities people look for in Wintergreen include tennis, a swimming pool and a garden. Whether you're vacationing with your besties, family or even pets, Vrbo vacation properties have the best amenities for beginning new traditions with the people you cherish the most.

Are there large group vacation rentals in Wintergreen?

Wintergreen has 102 vacation homes that can accommodate 10 or more guests. These properties come with all the space you need to enjoy good times with friends and family.

Are there vacation rentals in Wintergreen that welcome kids?

Gather your whole family for an epic adventure in Wintergreen at one of our 378 family-friendly vacation homes. Many of these stays come with conveniences that are great for getaways with the little ones, including kitchens, living rooms and swimming pools. Just click on the "Properties good for families" filter and choose your favorite option.

What are the top attractions for families in Wintergreen?

If you're craving some family-friendly entertainment close to the center of Wintergreen, head over to Stoney Creek Golf Course.

Are there one-bedroom vacation rentals in Wintergreen?

Wintergreen has 65 one-bedroom rentals on offer. Usually situated in desirable areas thanks to their compact size, a one-bedroom property is great if you're traveling with a friend or your partner. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back while exploring this fabulous destination.

Can I find two-bedroom vacation rentals in Wintergreen?

Pick from 82 two-bedroom vacation rentals in Wintergreen. Put your little ones in the second room or fill it with a couple of your favorite people. There's ample space for whoever's fortunate enough to be coming along for the ride.