Photo by Melissa Smestad

Wintergreen holiday lettings

We found 904 holiday rentals — enter your dates for availability

Select from 228 houses, 314 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:15 May - 22 May

Image gallery for Wintergreen Luxury, Best Views in VA!

Exterior
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Wintergreen Luxury, Best Views in VA!

Wintergreen Resort

12% off
Price is £8,061
for 7 nights, 1 chalet
£1,152 per night
includes taxes & fees
Wintergreen Luxury, Best Views in VA!

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 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.

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.

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

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.

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)
  • Lovingston Winery (11.5 mi / 18.5 km)
  • Pippin Hill Farm & Vineyards (14 mi / 22.6 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:

  • Reids Gap Trailhead (4.8 mi / 7.8 km)
  • Sherando Lake Recreation Area (6.5 mi / 10.5 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)
  • 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?
When considering a holiday rental in Wintergreen, Virginia, the area around the Wintergreen Resort is an excellent choice. This neighbourhood not only offers a variety of properties, often with stunning views of the Blue Ridge Mountains, but also provides easy access to a wealth of recreational activities. With a range of accommodations available, from cosy cabins to spacious condos, visitors can find something that suits their needs superbly.

Staying near Wintergreen Resort means you are just moments away from the resort's top attractions, such as the scenic ski slopes in winter and the beautiful hiking trails during the warmer months. The Appalachian Trail, which runs nearby, offers breathtaking vistas and a chance to immerse yourself in nature. Additionally, the resort features a golf course that appeals to enthusiasts looking to enjoy a round amidst picturesque surroundings.

Another appealing area is the nearby Rockfish Valley, which is known for its charm and tranquility. This location is ideal for those seeking a more laid-back atmosphere, yet it remains conveniently close to Wintergreen's attractions. With various properties available here, guests can relax in a peaceful setting while being just a short drive from the excitement of the resort.
How much does it cost to rent a holiday home in Wintergreen?
Prices for holiday 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 holiday 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 holiday rentals in Wintergreen?
A long-stay holiday rental in Wintergreen is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Wintergreen holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Wintergreen with parking available—perfect for families or travellers 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.
What are popular rental amenities in Wintergreen?
In Wintergreen, there are no specific popular rental amenities that stand out. The area primarily offers a variety of holiday rentals, including both apartments and private homes, but without popular amenities that are commonly sought after by travellers. Visitors can expect a range of basic facilities, but details on specific amenities are not prominent.
When is the best time to visit Wintergreen for a holiday rental?
January is the most popular time to visit Wintergreen, Virginia, particularly for those keen on winter sports. This month falls within the peak season, which spans from December to February, when the area transforms into a snowy wonderland ideal for skiing, snowboarding, and tubing. The resort's slopes are well-maintained, offering a thrilling experience for both beginners and seasoned enthusiasts.

During January, you can expect average temperatures around -1 to 4 degrees Celsius, superb for outdoor adventures. The crisp winter air makes it an invigorating time for visitors to enjoy not only the slopes but also other activities like snowshoeing and cosy evenings by the fire in your holiday rental.

If you're seeking a more tranquil experience, consider visiting in May, which marks the low season. This month provides a wonderful opportunity to enjoy the serene beauty of nature as spring blooms. Hiking trails become accessible, and the scenic views of the Blue Ridge Mountains are absolutely stunning without the bustling crowds.
How early should I book a Wintergreen holiday rental?
Book your Wintergreen holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wintergreen?
In Wintergreen, Virginia, visitors can enjoy a range of attractions that cater to both outdoor enthusiasts and those seeking relaxation. The Wintergreen Resort is a central highlight, offering skiing and snowboarding in the winter months, while the summer presents opportunities for hiking, mountain biking, and enjoying the scenic views of the Blue Ridge Mountains. Nearby, the Appalachian Trail provides extensive hiking routes for those looking to immerse themselves in nature.
Can I change or cancel my Wintergreen home rental booking on Vrbo?
To find Wintergreen holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More holiday ideas