Photo by Rebecca Brent

Wintergreen holiday lettings

We found 839 holiday rentals — enter your dates for availability

Select from 48 houses, 145 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.

Holiday rentals with weekly discounts - Wintergreen

Showing deals for:17 Oct - 24 Oct
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Why visit Wintergreen

  • Thrilling skiing adventures: Wintergreen is renowned for its excellent skiing facilities, perfect for both seasoned skiers and beginners.
  • Stunning natural scenery: The picturesque landscapes surrounding Wintergreen offer breathtaking views and opportunities for outdoor pursuits.
  • Charming accommodation options: Enjoy a range of delightful holiday rentals, from cosy cabins to modern condos, catering to all group sizes.
  • Rich cultural experiences: Explore local museums and historic houses that showcase the area's heritage and culture.
  • Family-friendly activities: The resort provides a variety of recreational activities ensuring fun for all ages.

Popular types of accommodation in Wintergreen

Wintergreen offers a delightful selection of holiday rentals, including houses, cosy cabins, and modern condos. Whether you're seeking a Wintergreen resort vacation rental for a family getaway or a romantic retreat, you'll find the perfect accommodation to suit your needs. With transparent pricing and helpful information, we ensure your stay is filled with reassurance and savings. Discover your ideal Wintergreen holiday rental today!

  • Houses: The top choice for visitors to Wintergreen, offering spacious and comfortable stays for families or groups.
  • Condos: A popular option for those desiring modern amenities and convenient access to local attractions.
  • Cabins: Ideal for a rustic getaway, perfect for nature enthusiasts seeking a tranquil escape.
  • Apartments: A versatile choice for couples or solo travellers, providing a home-like atmosphere.
  • Cottages: A charming option, perfect for a quaint and intimate holiday experience.**

Top attractions near Wintergreen

Wintergreen, Virginia, is a fantastic destination for skiing and adventure sports enthusiasts. Visitors can enjoy a range of activities at the Wintergreen Resort, including skiing, outdoor pursuits, and cultural experiences. Popular points of interest include the ski area, museums, and historic houses, catering to those seeking both thrill and relaxation. Whether you're after a winter getaway or friendly activities, Wintergreen offers an exhilarating escape into the great outdoors.

  • Wintergreen Resort: A premier ski resort offering thrilling winter sports and outdoor adventures, set against stunning mountain scenery. Enjoy activities like skiing, snowboarding, and hiking, making it perfect for both adrenaline junkies and families seeking fun.
  • Blue Ridge Parkway North Entrance: A fantastic visitor centre that serves as the gateway to the scenic Blue Ridge Parkway. Ideal for families, it offers outdoor activities, breathtaking views, and access to numerous walking trails.
  • Raven's Roost Overlook: An enchanting lookout spot providing romantic vistas and adventurous hiking opportunities. Perfect for couples and nature lovers, it offers stunning views of the surrounding landscape, especially at sunset.

Things to do recommended for couples

Planning a couple's getaway in Wintergreen? Enjoy thrilling skiing at Wintergreen Resort, indulge in wine tasting at Hill Top Berry Farm & Winery, or relish the romantic atmosphere at Veritas Vineyard and Winery. It's the perfect blend of adventure and relaxation for lovebirds!

Things to do recommended for families

Families will love the serene Sherando Lake Recreation Area, located 4.3km from Wintergreen. This tranquil spot offers wellness and relaxation vibes, perfect for a day of picnicking, hiking, or simply unwinding amid nature's beauty.

Things to do recommended for groups

Discover the delightful Bold Rock Hard Cider Nellysford Cidery for a taste of local brews, enjoy a round at Stoney Creek Golf Course for some sporty fun, or embark on an adventure at Reids Gap Trailhead, where stunning scenery awaits your group.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in and around Wintergreen

Wintergreen, Virginia, offers a delightful blend of adventure and relaxation for holidaymakers. Nestled in stunning scenery, this charming village is perfect for skiing and outdoor sports, while also providing cosy retreats for families. Nearby attractions enhance the experience, showcasing beautiful vistas and inviting holiday homes. Whether you're seeking recreation or a peaceful escape, Wintergreen promises a memorable getaway that caters to all tastes, making it an idyllic choice for your next vacation.

  • Nellysford: Situated a mere mile from Wintergreen, Nellysford is a charming town that draws visitors eager to embrace the outdoors. Known for its exhilarating skiing opportunities, this destination is perfect for those seeking adventure and sports experiences. From the picturesque ski fields to the well-equipped ski resort, Nellysford offers a winter wonderland for enthusiasts. Additionally, the nearby lake and the expansive national state park provide ample opportunities for hiking, picnicking, and nature exploration, making it a great spot to unwind and reconnect with nature.
  • Pedlars Edge: Nestled in close proximity to Wintergreen, Pedlars Edge is a delightful neighbourhood that thrives on its adventurous spirit. With easy access to ski resorts and fields, it’s an ideal base for skiing aficionados. The stunning landscape is complemented by a beautiful lake and the nearby national park, where outdoor activities abound. Whether you're hitting the slopes or enjoying a leisurely stroll in the national state park, Pedlars Edge is perfect for those looking to engage with Virginia's natural beauty while indulging in thrilling sports.
  • Treeloft: Another welcoming neighbourhood near Wintergreen, Treeloft is renowned for its adventure-centric offerings. Visitors flock to this area to take advantage of the excellent skiing facilities available at the local ski resorts and fields. The neighbourhood is surrounded by scenic landmarks, including a serene lake and a national park, which provide the perfect backdrop for outdoor escapades. Treeloft is an excellent choice for holidaymakers who wish to balance their skiing adventures with tranquil moments in nature.

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

What do I need to keep in mind when booking a vacation in 'Wintergreen

If you're travelling with a group, family, or pets, or if you're seeking longer stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Taking a trip with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Wintergreen: For many, a family getaway isn't truly fulfilling unless their furry companion is along for the ride. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Wintergreen: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a dedicated area to plan new getaways, pick up from where you last stopped, or view and organise your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Stoney Creek Golf Course (1.3 mi / 2.1 km)
  • 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)

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:

  • Sherando Lake Recreation Area (6.8 mi / 10.9 km)
  • 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)

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, February or March, when snowfall averages 3 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.
Are there holiday rentals with WiFi in Wintergreen?
Wintergreen has 149 holiday rentals with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Wintergreen?
Decide on your travel dates and then use the filters to look for holiday rentals with ac in Wintergreen on Vrbo. With 334 air-conditioned properties on offer here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday rental in Wintergreen?
It's a good idea to check with the Wintergreen holiday home you're looking at on Vrbo as the minimum age differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday rental in Wintergreen for?
It really depends on the Wintergreen property. To see all available options offering extended stays, simply type your travel dates and guest number into the Vrbo search page. Enjoy having the property to yourself, along with the comforts of home like a kitchen, air conditioning and an outdoor space where the kids can burn off energy. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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