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Wintergreen vacation rentals

We found 868 vacation rentals — enter your dates for availability

Select from 50 houses, 147 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.

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Find out more about Wintergreen

Find out more about Wintergreen

Why visit Wintergreen

  • Thrilling winter sports: Experience the excitement of skiing and snowboarding at Wintergreen's premier ski resort.
  • Breathtaking mountain views: Enjoy stunning scenic vistas while exploring the picturesque landscapes surrounding Wintergreen.
  • Family-friendly activities: Engage in a variety of outdoor adventures and fun activities suitable for all ages.
  • Cultural exploration: Discover local history through museums and historic houses in the charming village.
  • Diverse accommodations: Choose from cozy cabins, condos, and private homes for a comfortable stay.

Popular types of accommodation in Wintergreen

Wondering what types of accommodations await you in Wintergreen? Look no further. Our most popular options include Houses, cozy Condos, and charming Cabins. Whether you're seeking a Wintergreen resort experience or vacation rentals that offer stunning vistas, we have the perfect spot for you. Discover the ideal Wintergreen vacation rentals that provide both comfort and convenience for your getaway.

  • Houses: The top choice for visitors to Wintergreen, these spacious homes offer comfort and privacy for families and groups.
  • Condos: A popular option, condos provide a blend of convenience and amenities, ideal for couples and smaller groups.
  • Cabins: For a rustic getaway, cabins offer a cozy atmosphere surrounded by nature, perfect for relaxation.
  • Apartments: Affordable and practical, apartments are great for short stays, offering essential comforts.
  • Cottages: These charming rentals provide a quaint and intimate setting for a romantic retreat or peaceful escape.**

Top attractions near Wintergreen

Wintergreen, Virginia, is the perfect destination for ski and adventure enthusiasts. Visitors can enjoy a variety of attractions, including a ski resort, museums, and historic houses, all while immersing themselves in the culture and outdoor experiences the area has to offer. Whether you're looking for thrilling sports or a glimpse into local history, Wintergreen provides a memorable vacation for every traveler.

  • Wintergreen Resort: A premier ski resort offering thrilling winter sports, cozy lodgings, and vibrant outdoor activities. Enjoy breathtaking mountain views and adventure year-round, from skiing in the winter to hiking in the summer.
  • Blue Ridge Parkway North Entrance: A scenic visitor center that serves as a gateway to the famous Blue Ridge Parkway. Experience stunning natural beauty, engaging exhibits, and family-friendly outdoor adventures amid the picturesque landscapes.
  • Raven's Roost Overlook: A breathtaking lookout spot perfect for romantic sunsets and panoramic views. Enjoy tranquil moments in nature, ideal for couples seeking adventure and stunning vistas in a serene environment.

Things to do recommended for couples

Wintergreen, Virginia, offers a perfect romantic getaway for couples. Enjoy skiing at Wintergreen Resort, just 3 miles away, or indulge in wine tasting at Hill Top Berry Farm & Winery and Afton Mountain Vineyards, both offering charming atmospheres and stunning views within a short drive.

Things to do recommended for families

Families can explore the serene Sherando Lake Recreation Area, located 7 miles from Wintergreen. This beautiful spot offers wellness and relaxation, perfect for a day of picnicking, hiking, and enjoying nature together.

Things to do recommended for groups

Groups visiting Wintergreen can enjoy a tasting at Bold Rock Hard Cider, partake in a round at Stoney Creek Golf Course, and hike the scenic Reids Gap Trailhead for an outdoor adventure, making the most of the area's vibrant atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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 seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with amenities that suit their age, like a private pool. Additionally, you may want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many families, a trip isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you're searching for vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. 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 charming village perfect for ski and adventure enthusiasts. Visitors can enjoy family-friendly activities and breathtaking mountain views while exploring nearby cities and neighborhoods. Experience the stunning scenery and recreational opportunities that make this destination a relaxing mountain getaway. With a variety of vacation rentals and resort experiences, Wintergreen offers the ideal blend of outdoor excitement and tranquil surroundings for an unforgettable trip.

  • Nellysford: Nestled in the heart of Virginia, Nellysford serves as a gateway to Wintergreen Resort, making it a prime destination for ski enthusiasts and adventure seekers. This charming city offers a range of outdoor activities, from thrilling ski runs to scenic hikes in nearby national parks. Visitors can explore stunning lakes and take in the breathtaking views of the Blue Ridge Mountains. With its close proximity to ski fields and resorts, Nellysford is perfect for those looking to immerse themselves in a winter sports experience.
  • Treeloft: A cozy neighborhood surrounding Wintergreen, Treeloft is ideal for travelers seeking a peaceful retreat with easy access to skiing and outdoor adventures. The area is renowned for its ski slopes and beautiful landscapes, making it a popular choice for sports enthusiasts. With nearby lakes and national parks, visitors can engage in a variety of outdoor activities year-round. Treeloft combines the charm of a residential community with the excitement of winter sports, ensuring an unforgettable stay.
  • Pedlars Edge: Located around Wintergreen, Pedlars Edge is a delightful neighborhood that caters to those looking for adventure in a picturesque setting. Known for its ski resorts and fields, this area attracts visitors eager to hit the slopes or explore the natural beauty of the surrounding parks. With easy access to both lakes and national parks, Pedlars Edge provides ample opportunities for outdoor recreation. Whether you're skiing in winter or hiking in summer, this vibrant neighborhood is a perfect base for your adventures.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageSlightly Low
May64.0°F (17.8°C)Light RainMostly SunnyModerately LowAverage
June72.1°F (22.3°C)Light RainMostly SunnyModerately LowAverage
July76.6°F (24.8°C)Light RainMostly SunnyAverageSlightly Low
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 High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can lead to varying prices. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the total booking amount. Being the organizer truly has its benefits. Enroll in our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on eligible stays. Sign up today and start reaping the rewards.

Vrbo Trips: Effortless planning

Vrbo's unique Trip Board offers you a convenient way to plan new adventures, pick up where you last paused, or keep track of your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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.

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