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Wintergreen vacation rentals

We found 905 vacation rentals — enter your dates for availability

Select from 223 houses, 314 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:Jun 12 - Jun 19

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Find out more about Wintergreen

Why visit Wintergreen

  • Outdoor Adventures: Enjoy skiing on gentle slopes in winter or hiking through lush landscapes in summer, perfect for adventure seekers.
  • Wintergreen Resort: Experience a range of activities at the popular resort, including relaxation at the Wintergreen Spa.
  • Stunning Mountain Views: Immerse yourself in breathtaking views of Virginia’s mountains throughout the year.
  • Cozy Accommodations: Choose from private homes, charming cabins, and stylish condos tailored to your vacation needs.
  • Cultural Experiences: Explore local museums, historic houses, and the visitor center to enrich your visit.

Popular types of accommodation in Wintergreen

Discover the charm of Wintergreen with a variety of vacation rentals, including private homes, cozy cabins, and stylish condos. Whether you're looking for a winter getaway at Wintergreen Resort in Virginia or a relaxing retreat, our platform offers a selection of Wintergreen resort rentals tailored to your needs. Enjoy the beauty of Virginia's mountains while finding the perfect star-rated Wintergreen Resort condos for your stay. Your ideal vacation awaits.

  • Houses: These spacious homes are the top choice for travelers, offering comfort and amenities perfect for families or groups.
  • Condos: A popular option, condos provide a blend of convenience and community, ideal for those wanting a home-like atmosphere.
  • Cabins: Embrace nature in cozy cabins that offer a rustic retreat, perfect for outdoor enthusiasts.
  • Apartments: For a more urban vibe, apartments offer a stylish and convenient base for exploring Wintergreen.
  • Cottages: These charming, smaller dwellings provide an intimate setting for a romantic getaway or peaceful retreat.**

Top attractions near Wintergreen

Wintergreen, Virginia, is an ideal destination for ski and adventure enthusiasts, offering a variety of attractions such as the visitor center, historic houses, and museums. Visitors can enjoy cultural experiences and outdoor activities, with options like the Wintergreen Spa and the Wintergreen Resort, which features friendly activities and abundant outdoor adventures. Whether traveling solo or with family, Wintergreen promises a memorable vacation filled with excitement and relaxation.

  • Walton's Mountain Museum: Located 13 miles from Wintergreen, this charming museum celebrates the culture and history of the beloved television show The Waltons. Visitors can explore exhibits featuring memorabilia, photographs, and artifacts that bring the show's rural Virginia setting to life.
  • Rockfish Gap Entrance Shenandoah: Situated 11 miles away, this scenic entrance to Shenandoah National Park offers breathtaking views and outdoor adventures, including hiking, wildlife viewing, and picnicking amidst stunning natural beauty.
  • Blue Ridge Parkway North Entrance: Just 10 miles from Wintergreen, this visitor center serves as a gateway to the picturesque Blue Ridge Parkway, providing family-friendly activities, spectacular vistas, and opportunities for outdoor exploration.

Things to do recommended for couples

Wintergreen offers a perfect romantic getaway for couples. Enjoy a cozy cabin retreat, experience wine tasting at local vineyards, or take a scenic hike together. Don’t miss stargazing by the fireplace or a couples massage at a nearby spa for a truly relaxing experience.

Things to do recommended for families

Families will love hiking along the scenic trails of Wintergreen Resort, exploring the beautiful Blue Ridge Mountains. In winter, skiing and snowboarding are popular activities, while summer offers mountain biking and zip-lining for thrilling adventures together.

Things to do recommended for groups

Groups visiting Wintergreen can enjoy skiing and snowboarding on the slopes, hiking the beautiful trails in the Blue Ridge Mountains, and savoring local wines at nearby vineyards. Don't miss the stunning views from the mountain overlook, perfect for capturing memorable group photos.

*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 it’s with a group, family, pets, or for an extended stay, be sure to refine your search according to what matters most to you. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Wintergreen with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, you should think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many families, a vacation wouldn't feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you’re in search of vacation rentals that offer great deals 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 rental options. Don't forget to include additional amenities 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 haven for adventure seekers and families alike, offering stunning mountain views and lush landscapes. Visitors can immerse themselves in a winter wonderland on gentle slopes perfect for skiing or enjoy the vibrant summer scenery. Nearby cities provide a relaxing urban atmosphere, ensuring a well-rounded vacation experience filled with recreation and family-friendly activities. Whether you're skiing down the slopes or exploring the charming surroundings, Wintergreen promises unforgettable moments in nature.

  • Nellysford: Nestled in the breathtaking Blue Ridge Mountains, Nellysford is a charming city that serves as the gateway to Wintergreen Resort. This picturesque area is a haven for outdoor enthusiasts seeking thrilling ski adventures and sports experiences. The nearby ski fields and resorts offer top-notch facilities for skiing, snowboarding, and other winter sports. Visitors can also enjoy the stunning natural beauty of nearby landmarks, including the expansive national state park and serene lakes. Nellysford’s scenic surroundings make it perfect for hiking, biking, and exploring the great outdoors in every season.
  • Treeloft: Treeloft is a delightful neighborhood situated close to Wintergreen, offering a perfect blend of adventure and tranquility. This area attracts travelers eager for skiing and outdoor activities amidst stunning mountain vistas. With ski resorts and fields at your doorstep, Treeloft is an ideal base for winter sports enthusiasts. The proximity to beautiful lakes and national parks enhances the appeal, providing ample opportunities for hiking, fishing, and enjoying nature's serenity. Treeloft’s cozy atmosphere makes it a fantastic spot for families and friends looking to create lasting memories.
  • Pedlars Edge: Located nearby Wintergreen, Pedlars Edge is a welcoming neighborhood that invites visitors to immerse themselves in outdoor fun and adventure. Known for its ski offerings, this charming area boasts easy access to ski resorts and fields, making it a favorite among winter sports lovers. The surrounding natural beauty, including lakes and national parks, allows for year-round exploration, from skiing in the winter to hiking and picnicking in the summer. Pedlars Edge is an ideal retreat for those looking to experience the best of Virginia's outdoor lifestyle.

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 SunnyAverageAverage
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 LowSlightly Low
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 simple

Are you hoping to save on your upcoming trip? 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 aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll earn OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Become a part of our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on eligible stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your travel adventures. You can easily create new trips, resume your previous plans, or keep track of your organized itineraries. You'll find your saved or booked properties neatly categorized as Potential, Upcoming, or Current Trips. To begin using 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, Virginia, United States of America when booking a vacation rental?
For a delightful vacation rental experience in Wintergreen, Virginia, the area surrounding the Wintergreen Resort is an excellent choice. This neighborhood offers a variety of properties, from cozy cabins to spacious condos, suiting various group sizes and preferences. One of the top attractions here is the stunning Blue Ridge Mountains, which provide breathtaking views and a number of outdoor activities, including hiking and skiing, depending on the season.

Additionally, the nearby Stoney Creek area features lovely golf courses and scenic spots, superb for those looking to relax and enjoy the natural beauty. With access to amenities like restaurants and shops, as well as the famous Wintergreen Spa, this region truly offers a balanced mix of adventure and relaxation.
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.
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, Virginia, United States of America?
In Wintergreen, Virginia, visitors can enjoy a variety of attractions centered around outdoor activities and stunning natural beauty. The Wintergreen Resort is a key highlight, offering year-round recreational opportunities including skiing and snowboarding in winter, as well as hiking and mountain biking during the warmer months. The resort features scenic views of the Blue Ridge Mountains, making it a superb backdrop for outdoor enthusiasts.

The area also includes the Appalachian Trail, which provides excellent hiking options for those looking to explore the stunning landscapes and diverse wildlife. For a more relaxed experience, Lake Monocan offers opportunities for fishing, swimming, and picnicking, with facilities that cater to families.

In addition, the nearby Nelson County wineries present a chance for visitors to indulge in local wine tastings while enjoying the picturesque vineyard settings.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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