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Wintergreen vacation rentals

We found 839 vacation rentals — enter your dates for availability

Select from 48 houses, 145 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 17 - Oct 24
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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?
Pedlars Edge is one of the more in-demand locations to book a vacation home in Wintergreen. Make yourself at home here to enjoy the relaxation and comfort that comes with having a place all to yourselves.
What is the most popular type of vacation rental accommodation in Wintergreen?
Based on our data, condos are the most sought-after type of property in Wintergreen. But naturally, everyone's idea of an awesome trip will differ. Vrbo has vacation rentals of all sizes and shapes, and we'll help you discover your perfect match.
How much does it cost to rent a vacation rental in Wintergreen?
Several factors influence how much you'll pay for a vacation rental in Wintergreen, such as the type of property, season and length of stay. Still, all our vacation homes have something in common --- excellent value. Just enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Wintergreen?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Wintergreen travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to pick the amenities and features you want in your vacation home.
Are there pet-friendly vacation rentals in Wintergreen?
With 384 properties that allow pets, your furry best friend can join you on your Wintergreen getaway. Use the filter tool to browse our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Wintergreen?
Pack your swimming gear and pool noodle, because there are 248 houses with a private pool in Wintergreen. Settle in at one of these sought-after vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Wintergreen?
The most popular rental amenities people search for in Wintergreen include a nearby waterfront, a lake view and an electric car charging station. Whether you're going on vacation with family, your besties or even pets, Vrbo vacation properties come with the best amenities for ultimate relaxation with the people that matter most.
Are there large group vacation rentals in Wintergreen?
Wintergreen has 120 vacation homes that can host 10 or more guests. These properties come with the space and privacy you need to enjoy good times with your nearest and dearest.
Are there vacation rentals in Wintergreen that welcome kids?
Gather your entire family for a fun-packed adventure in Wintergreen at one of our 382 family-friendly vacation properties. These stays offer amenities that are ideal for trips with youngsters, like full kitchens, multiple bedrooms and swimming pools. Simply check the "Properties good for families" filter box and decide on your favorite.
What are the top attractions for families in Wintergreen?
Plan a day out with the family at Wintergreen Resort. This popular attraction is within easy reach of the heart of Wintergreen.
Are there one-bedroom vacation rentals in Wintergreen?
Yes, Wintergreen has 68 one-bedroom rentals on offer. Typically located in popular areas because of their compact size, a one-bedroom property is ideal if you're traveling with your partner or a pal. And with home comforts such as air conditioning and more privacy than a standard hotel, you'll be able to chill out while exploring this awesome destination.
Can I find two-bedroom vacation rentals in Wintergreen?
Wintergreen has 79 two-bedroom vacation properties to select from. Find a vacation home with all the comfort and space you want at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in Wintergreen?
Whether you want to keep up with world events, check emails or surf social media, there are 150 vacation homes with WiFi in Wintergreen. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Wintergreen?
Wintergreen has 335 vacation rentals where you'll be able to unwind in air-conditioned comfort. To locate a stay on Vrbo with this perk, enter your preferred travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Wintergreen?
The minimum age is normally 16, 18 or 21. It can differ from property to property on Vrbo, so check the rules of your preferred Wintergreen stay before booking your escape.
How long can I rent a vacation rental in Wintergreen for?
It's down to the Wintergreen property. To view all available options offering extended stays, simply type your dates and number of people into Vrbo's search page. Enjoy having the entire property to yourself, along with comforts such as a full kitchen, air conditioning and a yard where the little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Wintergreen?
In Wintergreen, you'll find some great deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're off on a mini escape or an extended stay, we offer a variety of options to match your style.

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