Discover a selection of 500 vacation rentals in Wintergreen that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $89 per night, and houses and cabins are popular options for a stay in Wintergreen. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Wintergreen
Destination guide

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.

Things to do

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.

Day trips

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.

Natural features

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.

How to get there

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.

What are the top vacation rentals in or near Wintergreen?

Whether you're seeking an intimate escape for you and your special someone or a sprawling house to fit family and friends, you'll find some top vacation rentals in and around Wintergreen. Here are a couple to start you off:

  • Around 2 miles from the center of Wintergreen, you'll love staying at "Reconnect With Family And Friends At Our Large". It has 6 bedrooms and a range of conveniences like lowered locks and an ice maker.
  • "Come To The Blue Ridge For Springtime. . . Amazing Views And 5" is another top pick, offering 2 bedrooms, optional golf privileges, a fireplace and more. It's around 2 miles from Wintergreen.

For even more great options, use the search bar at the top of the page to find the perfect Wintergreen vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Wintergreen?

Clock off on Friday and then forget the real world. If you're ready for some fun and relaxation, these retreats in and near Wintergreen promise an unforgettable weekend getaway:

  • "Beautiful Mountain Views, Steps To Slopes" is an excellent option around 2 miles northwest of central Wintergreen. You'll never have to wander far to find something to do around this property. Get outdoors and visit Goshen Pass Natural Area Preserve and Raven's Roost Overlook. Activities like ice skating and cycling will add a nice touch to your weekend trip.
  • "Wintergreen Retreat - New Luxury Post And Beam Home" is another great property to consider. Around 2 miles northwest of Wintergreen, use it as a base to do a little kayaking or golf. Biscuit Run State Park and Raven's Roost Overlook also have to be on your itinerary if you stay here.

Can I find studio apartments for rent in and around Wintergreen?

Studio apartments may be on the smaller side, but they sure pack a punch when it comes to location and convenience. Make yourself comfortable at one of these welcoming studio apartments in and around Wintergreen:

  • Enjoy some time out on your own or take a few buddies along to "Wintergreen Five Star Rated One Bedroom Condo At Affordable Prices". You'll have plenty of amenities to take advantage of, including nearby hunting activities and an ice maker.
  • Another cool rental is "Ski In Ski Out Next To Mountain Inn". Don't be fooled by its modest size — this cozy apartment is loaded with handy amenities like free WiFi, outdoor furniture and lots more.

Can I find short term rentals in or near Wintergreen?

Yes, you'll find a selection of short-term rentals in and around Wintergreen. And best of all, Vrbo has something for all styles and budgets — from generous-sized homes for all the family to exquisite cottages made for two. Here's just a taste of what's on offer here:

  • Conveniently situated near attractions like Bold Rock Hard Cider Nellysford Cidery, "Enjoy An Appalachian Spring. . . Awesome Views And 5" will make the ideal home away from home during your stay in Wintergreen.
  • "Wintergreen Pet - Friendly Condo Near To Mountain Inn And Slopes" is another fantastic property that welcomes short-term guests. Make the most of your whirlwind visit by taking a look at local sights, including Stoney Creek Golf Course.

What are the best romantic weekend getaways in or near Wintergreen?

Nothing says "I love you" quite like a romantic weekend trip. If you'd like to spend a couple of relaxing evenings away with your partner, we've got some romantic getaways in and around Wintergreen that will get your heart racing:

  • Sneak off on Friday for a few passion-filled evenings at "Reconnect With Family And Friends At Our Large". Located roughly 2 miles from Wintergreen, this property comes with lots of nice touches, like a fireplace and a resort.
  • Another place where you can spend a few precious days together is "Come To The Blue Ridge For Springtime. . . Amazing Views And 5". Located around 2 miles from Wintergreen, winery tours and beauty services add to the ambiance here.

What are the best large group vacation rentals in or near Wintergreen?

Vacation with others and have twice as much fun. Whether you're planning an active escape with your besties or a big family gathering, there's no shortage of large group vacation rentals in and near Wintergreen:

  • A wealth of amenities including a firepit and a kitchen make "Reconnect With Family And Friends At Our Large" a group favorite. This getaway has 6 bedrooms and accommodates up to 16 guests. From the center of Wintergreen, it's around 2 miles away to the north.
  • Invite up to 12 of your favorite people to "Wintergreen Retreat - New Luxury Post And Beam Home" and fill the place with love and laughter. This popular option has 4 bedrooms and is around 2 miles to the northwest of central Wintergreen. It's packed with features to keep your large group comfortable, such as mountain views and a fireplace.

What are the best houses for rent with a pool in or near Wintergreen?

Nothing says fun times like a pool. Blow up your inflatable doughnut and browse these houses in or near Wintergreen that feature this vacation essential:

  • Round up your crew and enjoy an unforgettable break at "Fantastic Mountain And Valley Views From House And Deck". There's a lot to love about this escape apart from its pool, such as a TV and cable/satellite TV services.
  • Alternatively, unpack your suitcase at "5 Bedroom Wintergreen House With Game Room". Along with a refreshing pool, you can also make use of free toiletries and a dining table.

Not sure what the weather is like in Wintergreen? It has a humid subtropical climate, with average temperatures in summer ranging from 65 ºF to 85 ºF. If you're searching for a little more inspiration on where to stay in this amazing destination, use the search bar at the top of the page and adjust the filters to browse through our entire selection of Wintergreen vacation rentals.

What are the best large family vacation rentals in or near Wintergreen?

You love your family of course, but that doesn't mean you all have to pack together like sardines on vacation. Take no chances and book a large family vacation rental in or around Wintergreen where you can spread out and relax:

  • Make fun vacation memories at "Reconnect With Family And Friends At Our Large". With 6 bedrooms sleeping up to 16 guests, this roomy retreat is around 2 miles north of Wintergreen. There are loads of amenities to make use of here, such as a smart TV and outdoor furniture.
  • Another comfortable family escape is "Wintergreen Retreat - New Luxury Post And Beam Home". Around 2 miles northwest of Wintergreen, it features 4 bedrooms, room for up to 12 guests, nearby ecotour services and a stereo.

Can I find family cabin rentals in or near Wintergreen?

Time spent with family is priceless, which is why we'll help you find a place where you can truly connect. Stay in one of these family cabin rentals in or near Wintergreen and create wonderful memories with the people you love:

  • "4 Bedroom Cabin Mins To Trails And Breweries Pets Welcome" - This popular getaway offers a dining table and a toaster and is located approximately 2 miles to the northwest of the center of Wintergreen.
  • "Evolve | Creekside Cabin In Wintergreen Resort" - This cabin has also been designed with families in mind and is around 2 miles northwest of Wintergreen. Offering a toaster, a barbecue grill and more, it'll get your group's tick of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Wintergreen vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Wintergreen?

Add an extra touch of indulgence to your vacation by booking someplace with an indoor pool. These large houses in or near Wintergreen have a swimming space that's all your own, along with ample room for whoever is lucky enough to be coming along:

  • Stay at "Holiday Home Casa La Carruba With Garden" and spend your days lazing poolside. This roomy retreat has 5 bedrooms sleeping up to 12 guests and a range of other great amenities. A sauna and a swimming pool are among them.
  • Alternatively, escape to "Luxurious New 4bedroom House: Ski, Hike", which has 4 bedrooms and caters for up to 10 guests. Along with that chic pool at your fingertips, a garden and a swimming pool will keep everybody happy and comfortable.

Want to see a few more options? Find your ideal stay by using the search bar at the top of the page. Simply adjust the filters to find the Wintergreen vacation rental that's perfect for you.