Photo by Rebecca Brent

Wintergreen holiday lettings

We found 894 holiday rentals — enter your dates for availability

Select from 228 houses, 312 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:6 Mar - 13 Mar

Image gallery for Majestic Mtn Cabin w sunset view & quick hiking access

Exterior
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Majestic Mtn Cabin w sunset view & quick hiking access

Wintergreen, VA

8% off
Price is £2,447
for 7 nights, 1 chalet
£350 per night
includes taxes & fees
Majestic Mtn Cabin w sunset view & quick hiking access

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    Enjoy full kitchens, pools, gardens and more

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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:

  • 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?
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.

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