Photo by Rebecca Brent

Wintergreen holiday lettings

We found 833 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 52 houses, 160 flats and other holiday rentals to find the perfect place for your stay in Wintergreen. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting scenic Wintergreen

Enjoy the wineries and other features of Wintergreen. Travellers to this scenic city praise the mountain views, skiing and hiking. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Wintergreen

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Wintergreen has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wintergreen Resort (3.2 mi / 5.1 km)
  • Afton Mountain Vineyards (8.9 mi / 14.3 km)
  • Veritas Vineyard and Winery (9.5 mi / 15.4 km)
  • Pippin Hill Farm & Vineyards (14 mi / 22.6 km)
  • King Family Vineyards (15.4 mi / 24.7 km)
  • Stoney Creek Golf Course (1.3 mi / 2.1 km)

Exploring the natural landscape of Wintergreen

Whether you're an adventurous traveller or just want to appreciate the scenery, Wintergreen is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Crabtree Falls (10.1 mi / 16.3 km)
  • Blue Ridge Parkway North Entrance (10.3 mi / 16.6 km)
  • Rockfish Gap Entrance Shenandoah (10.8 mi / 17.4 km)
  • Reids Gap Trailhead (4.8 mi / 7.8 km)
  • Humpback Rocks (5.3 mi / 8.5 km)
  • Sherando Lake Recreation Area (6.8 mi / 10.9 km)

Seasonal weather averages in Wintergreen

Travellers enjoy Wintergreen for its skiing. If you've planned your trip around snowy activities, consider visiting in January, December, March or February, when snowfall averages 4 cm and temperatures average 4°C.

Travelling to and around Wintergreen

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

Frequently asked questions

What is the best area to stay in Wintergreen when booking a holiday rental?

Pedlars Edge is one of the more desired locations to book a holiday home in Wintergreen. Settle in here and enjoy all the privacy and convenience that comes with having a place all to yourself.

What is the most popular type of holiday rental accommodation in Wintergreen?

Condos are the most popular type of holiday rental in Wintergreen, according to our data. Even if you've got a different vision in mind, Vrbo has holiday homes in a variety of shapes and sizes. Explore our options to find your ideal match.

How much does it cost to rent a holiday rental in Wintergreen?

Different factors affect how much you'll pay for a holiday rental in Wintergreen, like the time of year, property type and length of stay. However, all of our holiday homes have one thing in common — exceptional value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Wintergreen?

The average price for a holiday rental by the beach in Wintergreen depends on when you're travelling and the size and style of property you're looking for. Find prices easily on Vrbo by entering your travel dates. Then use the handy filters to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.

Are there pet-friendly holiday rentals in Wintergreen?

Pack a travel bag and a bone for the pup in your life because Wintergreen has 378 properties that open their doors to pets. Let your furriest pal enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.

Can I rent a house with a pool in Wintergreen?

Tick the "pool" box in our handy filter tool and choose from 236 houses with private pools in Wintergreen on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your Vrbo holiday home has its own swimming pool.

What are popular rental amenities in Wintergreen?

Some of the most popular rental amenities people look for in Wintergreen include tennis, a swimming pool and a garden. Whether you're holidaying with your besties, family or even pets, Vrbo holiday properties have the best amenities for beginning new traditions with the people you cherish the most.

Are there large group holiday rentals in Wintergreen?

Wintergreen has 102 holiday homes that can accommodate 10 or more guests. These properties come with all the space you need to enjoy good times with friends and family.

Are there holiday rentals in Wintergreen that welcome kids?

Gather your whole family for an epic adventure in Wintergreen at one of our 378 family-friendly holiday homes. Many of these stays come with conveniences that are great for getaways with the little ones, including kitchens, living rooms and swimming pools. Just click on the "Properties good for families" filter and choose your favourite option.

What are the top attractions for families in Wintergreen?

If you're craving some family-friendly entertainment close to the centre of Wintergreen, head over to Stoney Creek Golf Course.

Are there one-bedroom holiday rentals in Wintergreen?

Wintergreen has 65 one-bedroom rentals on offer. Usually situated in desirable areas thanks to their compact size, a one-bedroom property is great if you're travelling with a friend or your partner. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back while exploring this fabulous destination.

Can I find two-bedroom holiday rentals in Wintergreen?

Pick from 82 two-bedroom holiday rentals in Wintergreen. Put your little ones in the second room or fill it with a couple of your favourite people. There's ample space for whoever's fortunate enough to be coming along for the ride.

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