Photo by Rebecca Brent

Wintergreen vacation rentals

We found 848 vacation rentals — enter your dates for availability

Select from 50 houses, 143 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.

Vacation rentals with weekly discounts - Wintergreen

Showing deals for:Oct 31 - Nov 7
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Wintergreen

Find out more about Wintergreen

Why visit Wintergreen

  1. Thrilling skiing: Wintergreen is a premier destination for skiing and snowboarding, perfect for winter sports enthusiasts.
  2. Outdoor adventures: Enjoy hiking, mountain biking, and family-friendly excursions in the beautiful surrounding parks.
  3. Breathtaking scenery: Experience stunning views and picturesque landscapes that enhance your vacation experience.
  4. Cozy accommodations: Choose from a variety of vacation rentals, including condos and private homes for a comfortable stay.
  5. Local culture: Explore nearby historic sites, colleges, and charming neighborhoods for a taste of local heritage.

Popular types of accommodation in Wintergreen

Planning a getaway to Wintergreen? Discover the perfect place to stay with a variety of vacation rentals that cater to your needs. From cozy apartments and spacious houses to inviting condos at Wintergreen Resort, you’ll find accommodations that offer comfort and convenience. Enjoy the beauty of the mountains and easy access to outdoor activities while enjoying the transparency and savings our platform provides. Explore your Wintergreen vacation rental options today!

  • Apartments: The top choice for vacation rentals in Wintergreen, offering modern amenities and convenient locations for your stay.
  • Houses: A popular option providing spacious accommodations, ideal for families or groups looking for a home-away-from-home experience.
  • Condos: These stylish residences are a favored choice, blending comfort with stunning mountain views.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats offer a cozy escape in the woods.
  • Cottages: A charming option for those seeking a quaint and intimate getaway.**

Top attractions in Wintergreen

Wintergreen, Virginia, is an ideal destination for ski and adventure enthusiasts, offering a range of activities for outdoor and family experiences. Explore the stunning national and state parks, historic houses, and colleges nearby. For a well-rounded trip, consider seeking out local guides and top attractions to maximize your adventure. Wintergreen promises a memorable vacation filled with culture, recreation, and breathtaking scenery.

  1. Wintergreen Resort: Nestled only 3 miles from Wintergreen, this ski resort offers thrilling outdoor adventures year-round. Enjoy skiing, snowboarding in winter, and hiking or mountain biking during warmer months, all set against the beautiful backdrop of the Blue Ridge Mountains.
  2. Blue Ridge Parkway North Entrance: Located 10 miles away, this visitor center is perfect for families seeking adventure. Explore scenic trails, picnic areas, and interactive exhibits that celebrate the natural beauty and cultural heritage of the region.
  3. Rockfish Gap Entrance Shenandoah: About 11 miles from Wintergreen, this national park entrance invites you to experience breathtaking scenery and abundant wildlife. Enjoy hiking, picnicking, and stunning views that showcase the diverse ecosystems of the Appalachian Mountains.

Things to do recommended for couples

For a romantic getaway in Wintergreen, enjoy skiing at Wintergreen Resort, just 3 miles away. Savor delightful wines at Hill Top Berry Farm & Winery and Veritas Vineyard and Winery, both offering enchanting atmospheres and entertainment, perfect for couples looking to create lasting memories together.

Things to do recommended for families

Families can unwind at Sherando Lake Recreation Area, located 7 miles from Wintergreen. With its serene environment, this spot offers opportunities for picnicking, hiking, and swimming, making it perfect for relaxation and outdoor fun together.

Things to do recommended for groups

Groups visiting Wintergreen can enjoy a refreshing tour at Bold Rock Hard Cider for a taste of local brews, play a round at Stoney Creek Golf Course amidst beautiful scenery, and embark on a scenic adventure along the Reids Gap Trailhead for breathtaking views.

What do I need to keep in mind when booking a vacation in Wintergreen

When planning your trip—whether you're traveling with a group, family, pets, or looking for extended stays—be sure to use the right filters to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many families, a trip wouldn’t feel complete without their furry companion. If that resonates with you, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Wintergreen: If you're searching for vacation rentals that offer discounts for month-long stays, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Wintergreen

Wintergreen, Virginia, is a paradise for outdoor enthusiasts and adventure seekers. Nestled in the mountains, this winter vacation haven offers thrilling skiing and sports activities, along with family-friendly excursions. Nearby cities and neighborhoods provide a relaxing atmosphere, perfect for unwinding after a day of exploration. Whether you're hitting the slopes or enjoying the stunning scenery, Wintergreen promises a memorable getaway filled with friendly faces and unforgettable experiences.

  • Charlottesville: Located approximately 25 miles from Wintergreen, Charlottesville is a vibrant city known for its rich history and stunning outdoor scenery. Visitors can explore the historic University of Virginia, a UNESCO World Heritage site designed by Thomas Jefferson. The surrounding area offers ample opportunities for outdoor adventures, including hiking in nearby national parks and enjoying the serene beauty of local lakes. With a thriving arts scene, excellent dining options, and charming downtown shops, Charlottesville provides a perfect blend of culture and recreation for travelers.
  • Pedlars Edge: Nestled around Wintergreen, Pedlars Edge is a hidden gem for outdoor enthusiasts and sports lovers. This neighborhood is particularly famous for its ski activities, featuring well-maintained ski fields and resorts that cater to all skill levels. Beyond skiing, visitors can explore nearby national parks and lakes, making it an ideal spot for year-round adventures, whether it’s hitting the slopes in winter or enjoying picturesque hikes in summer. With its breathtaking mountain views and recreational offerings, Pedlars Edge is a must-visit for active travelers.
  • Treeloft: Treeloft is another charming neighborhood close to Wintergreen, attracting those seeking adventure and sports activities. Like its neighbor, Pedlars Edge, Treeloft is known for its excellent ski resorts and fields, making it a prime destination for winter sports enthusiasts. In addition to skiing, the area boasts access to beautiful parks and lakes, perfect for hiking, fishing, and enjoying nature. With its cozy atmosphere and proximity to winter sports, Treeloft offers visitors a delightful retreat in the heart of Virginia’s scenic landscape.

Best time to go to Wintergreen

If you're planning a trip to Wintergreen, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from December to February, while off-peak times, like May to June and August tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January33.4°F (0.8°C)Light RainMostly SunnyModerately HighSlightly High
February37.2°F (2.9°C)Light RainMostly SunnyModerately HighSlightly High
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
May64.0°F (17.8°C)Light RainMostly SunnyModerately LowSlightly High
June72.1°F (22.3°C)Light RainMostly SunnyModerately LowSlightly Low
July76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
August74.3°F (23.5°C)Light RainMostly SunnyModerately LowAverage
September68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly SunnyModerately HighSlightly Low

Booking with Vrbo is simple

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, take advantage of our filtering options to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. It truly pays off to be the organizer! By enrolling in our travel rewards program, One Key, you can immediately access exclusive member savings and earn OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient area for you to plan new trips, continue with your existing arrangements, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Alpine fun at Wintergreen vacation home rentals

An idyllic haven on the eastern slopes of the Blue Ridge Mountains, Wintergreen offers one-of-a-kind serenity and relaxation. Travelers are promised sweeping views of rippling streams, lush forests, and snow-tipped peaks from the doorstep of their Wintergreen vacation rental, but there’s more than just views on the itinerary. The 4-season Wintergreen Resort offers an unparalleled range of amenities to help you make the most of your peaceful retreat. You can chill out at the full-service spa, hit the links on one of 2 championship golf courses, or head for the great outdoors with winter snowboarding or summer hikes.

Tourist attractions near Wintergreen vacation rentals

The Rockfish Valley’s diverse ecosystem is proudly showcased at the Rockfish Valley Foundation Natural History Center, which is located within walking distance of most central Wintergreen vacation rentals. Open weekends between April and December, this center works to educate visitors on the historical and ecological features of the area. Their displays include a number of preserved native specimens, including black bears and wild turkeys, as well as collections of pelts, rocks, and other artifacts. Some of its most striking exhibits are on loan from the Virginia Museum of Natural History.

Things to do near Wintergreen vacation homes

The Wintergreen Resort is a major draw for winter sports enthusiasts, who flock here during the colder months to partake in snow tubing, skiing, and snowboarding. The Plunge is a 900 ft snow-tubing hill with 10 lanes and a 100 ft vertical drop. You can reach speeds of up to 40 mph as you whizz past some of the area’s most gorgeous scenery. Twenty-six slopes and 5 lifts making skiing another must in Wintergreen; the 129 acres of skiable terrain cater to all experience levels and 14 slopes are even lit up for night skiing, offering a new perspective on the landscape.

Best excursions near Wintergreen vacation homes

Wintergreen is the ideal base camp to explore the sights of Charlottesville. Vacation homes are available near places like the Virginia Discovery Museum, a children’s museum with interactive exhibits on history and science, and the Rotunda, an iconic university building with notable architecture. You could also visit the Fralin Museum of Art at the University of Virginia, a large museum housing an extensive collection of artwork from different cultures and time periods, and McIntire Park, a city park with woods, streams, and recreational areas.

Climate during your stay in Wintergreen vacation homes

The resort’s popularity as a snow-sports destination means that Wintergreen vacation rentals are in high demand throughout the winter months. Temperatures are low, with averages falling to 34°F in January, while natural snowfall is bolstered by state-of-the-art snow-making machines. The mercury rises when summer rolls around, with July temperatures hovering around 75°F. Mountain breezes keep things cool, however, and artificial snow is in constant supply, so you'll still be able to hit the slopes. Due to this unique 4-season appeal, vacation rentals in Wintergreen are perennially in vogue.

Blaze the Wintergreen trails

Part of the Virginia Birding and Wildlife Trail, the Rockfish River Loop Trail spans 6 miles and is a perfect spot for nature enthusiasts and bird-watchers to discover Virginia’s picturesque beauty. These trails also allow leashed dogs, so if you’re staying in a pet-friendly Wintergreen vacation rental, why not treat man’s best friend to a day out of their own? The Nelson Scenic Loop, meanwhile, is a 50-mile drive around Rockfish Valley that offers awe-inspiring views of the Blue Ridge Mountains, Crab Tree Falls, and the Appalachian Trail. Farmers markets, breweries, and wineries line the circular route, while spurs lead to hiking, biking, and birding trails.

Traveling to and around Wintergreen

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

Frequently asked questions

What is the best area to stay in Wintergreen when booking a vacation rental?
When booking a vacation rental in Wintergreen, Virginia, one of the best areas to consider is the Wintergreen Resort area itself. This picturesque neighborhood offers a fantastic blend of natural beauty and recreational activities, making it a superb spot for both relaxation and adventure. With over 300 properties available, including cozy cabins and luxurious condos, you'll have plenty of options to choose from.

Staying at Wintergreen Resort puts you in close proximity to some incredible attractions. The resort is renowned for its skiing and snowboarding opportunities during the winter months, with well-maintained slopes that cater to all skill levels. In the warmer months, the area transforms into a haven for hiking enthusiasts, with trails that lead through stunning landscapes and offer breathtaking views of the Blue Ridge Mountains. Additionally, the nearby Stoney Creek Golf Course is a favorite among golf lovers, providing a beautiful course set against a backdrop of rolling hills.

Another appealing aspect of the Wintergreen area is its proximity to the Blue Ridge Parkway, a scenic drive that showcases the region's stunning vistas and natural beauty.
How much does it cost to rent a vacation home in Wintergreen?
Prices for vacation rentals in Wintergreen vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wintergreen to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wintergreen vacation house rentals?
You can find great discounts on house rentals in Wintergreen on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Wintergreen?
A long-stay vacation rental in Wintergreen is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Wintergreen vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wintergreen with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Wintergreen for a vacation rental?
January is the most popular time to visit Wintergreen, Virginia, particularly for those seeking winter sports adventures. The peak season spans from December to February, when skiers and snowboarders flock to the slopes, making the most of the region's impressive snow conditions and well-groomed trails. With average temperatures ranging from the low 20s to mid-40s Fahrenheit, visitors can enjoy a crisp winter ambiance while participating in outdoor activities like skiing, snowboarding, and snowshoeing.

Wintergreen offers a variety of nearby attractions, such as scenic hiking trails, charming local shops, and cozy dining options, ensuring a well-rounded experience for all types of travelers. The resort's family-friendly atmosphere makes it an ideal destination for those looking to create lasting memories with loved ones.

For travelers seeking a more budget-friendly experience, May is a wonderful month to consider. This shoulder season not only offers pleasant spring weather, with temperatures typically hovering in the 50s and 60s Fahrenheit, but also provides opportunities for hiking and exploring the lush landscape as nature awakens.

Ultimately, the best time to visit Wintergreen for a vacation rental hinges on your preferences—whether you desire the excitement of winter sports during peak season or the peaceful charm of springtime exploration in the quieter months.
How early should I book a Wintergreen vacation rental?
Book your Wintergreen vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wintergreen?
In Wintergreen, Virginia, visitors can enjoy a range of outdoor attractions, especially for those who appreciate nature and outdoor activities. The Wintergreen Resort is a major highlight, offering skiing and snowboarding in winter and hiking and mountain biking trails in warmer months. The Blue Ridge Parkway, which is nearby, provides breathtaking scenic views and access to numerous hiking trails, including those leading to stunning waterfalls. For families, the area around Lake Monacan features swimming, fishing, and picnic spots, making it a superb day-out destination.
Can I change or cancel my Wintergreen home rental booking on Vrbo?
To find Wintergreen vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Wintergreen vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Rentals ideas

People also search for