Wintergreen holiday lettings

We found 935 holiday rentals — enter your dates for availability

Select from 224 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:25 Sept - 2 Oct

Image gallery for Majestic Mtn Cabin w quick hiking & overlook access

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

Majestic Mtn Cabin w quick hiking & overlook access

Nellysford

7% off
Price is £2,146
for 7 nights, 1 chalet
£307 per night
includes taxes & fees
Majestic Mtn Cabin w quick hiking & overlook access

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Why visit Wintergreen

  • Year-Round Outdoor Activities: Enjoy skiing in winter and hiking during warmer months, making Wintergreen a haven for adventure seekers.
  • Breathtaking Natural Scenery: Explore the stunning landscapes of the Blue Ridge Mountains, perfect for photography and relaxation.
  • Family-Friendly Atmosphere: The village offers numerous family-oriented excursions amidst picturesque surroundings.
  • Cultural Experiences: Discover local history through museums and historic houses, enriching your visit.
  • Cozy Accommodations: Choose from charming cabins, private homes, and modern condos for a comfortable stay.

Popular types of accommodation in Wintergreen

Welcome to Wintergreen, Virginia, a charming mountain retreat nestled in the Blue Ridge Mountains. Known for its stunning natural beauty, Wintergreen offers a variety of attractions, from scenic hiking trails to winter sports at the local resort. Whether you prefer houses, cosy cabins, or modern condos, you'll find the perfect accommodation to suit your needs. Experience the tranquillity and adventure that Wintergreen has to offer, all while enjoying the comforts of home.

  • Houses: The most sought-after accommodation in Wintergreen, offering spacious and comfortable living, perfect for families or larger groups.
  • Condos: A popular choice for couples and small families, providing modern amenities and often stunning views of the surrounding landscape.
  • Cabins: Ideal for those seeking a rustic charm, these cosy retreats immerse you in nature while offering essential comforts.
  • Apartments: Convenient and stylish, apartments are great for those who prefer a home-like environment with easy access to local attractions.
  • Cottages: Quaint and charming, cottages offer a peaceful getaway, perfect for a romantic escape or a tranquil family holiday.**

Top attractions near Wintergreen

Wintergreen, Virginia, is a delightful destination for outdoor enthusiasts and adventure seekers. Renowned for its skiing opportunities, this charming area also boasts rich cultural experiences, including museums and historic houses. Visitors can explore the stunning landscapes of nearby national and state parks, perfect for hiking and outdoor activities. Whether you seek thrilling sports or a taste of local history, Wintergreen offers a variety of attractions that cater to every traveller's interests.

  • Walton's Mountain Museum: This charming museum celebrates the legacy of the beloved TV series The Waltons, featuring memorabilia, exhibits on local history, and a glimpse into rural life in Virginia.
  • Rockfish Gap Entrance Shenandoah: A gateway to stunning outdoor adventures, this area offers breathtaking views, hiking trails, and opportunities for wildlife spotting in the beautiful Shenandoah National Park.
  • Crabtree Falls: Known as one of the tallest waterfalls in Virginia, this picturesque site features cascading waters, scenic hiking trails, and a romantic atmosphere, perfect for nature lovers.

Things to do recommended for couples

Wintergreen offers a charming escape for couples. Enjoy a scenic hike through the Blue Ridge Mountains, followed by a cosy evening by the fireplace at a local lodge. Don’t miss the stunning views from the mountain top, perfect for a romantic sunset together.

Things to do recommended for families

Your family will delight in the scenic hiking trails at Wintergreen Resort, perfect for all ages. Enjoy the thrill of mountain biking or take a leisurely stroll through the beautiful Blue Ridge Mountains. Don’t miss the seasonal activities, such as skiing in winter, for a truly memorable experience.

Things to do recommended for groups

Groups visiting Wintergreen can enjoy exhilarating outdoor activities such as skiing and snowboarding in winter, while summer offers hiking trails with breathtaking views and beautiful waterfalls. Don't miss the chance to sample local wines at nearby vineyards for a delightful group experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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 seeking longer stays, be sure to refine your search according to your key priorities. Here are some helpful booking tips for 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 filter for all these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Journeying with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many, a family getaway feels incomplete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone, including your four-legged friend, feels completely at home.
  • Planning for a long term stay visiting Wintergreen: If you’re in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Wintergreen

Wintergreen, Virginia, is a charming village perfect for adventure and relaxation. Nestled in verdant forests, it offers a plethora of outdoor activities, from skiing in winter to hiking in warmer months. Families can enjoy excursions amidst stunning scenery, while those seeking recreation will find ample opportunities to unwind. The inviting atmosphere and family-friendly vibe make Wintergreen an ideal destination for a memorable getaway.

  • Nellysford: Nestled in the heart of Virginia, Nellysford is a charming city that serves as a gateway to Wintergreen Resort. Known for its stunning natural beauty, this area offers a plethora of outdoor adventures, particularly for skiing enthusiasts. Visitors can enjoy exhilarating runs at the ski resort or engage in various sports activities. Nearby attractions such as the breathtaking national parks and serene lakes provide ample opportunity for exploration and relaxation. Whether you're hitting the slopes or taking in the scenic views, Nellysford promises an unforgettable experience.
  • Chestnut Springs: Chestnut Springs is a picturesque neighbourhood located close to Wintergreen, perfect for those seeking an adventurous getaway. Renowned for its winter sports, including skiing and snowboarding, Chestnut Springs is a hub for thrill-seekers. The area is surrounded by beautiful landscapes, including lakes and national state parks, ideal for hiking and picnicking in the warmer months. With its blend of outdoor recreation and tranquil surroundings, Chestnut Springs is an excellent choice for visitors looking to immerse themselves in nature.
  • Pedlars Edge: Another delightful neighbourhood near Wintergreen, Pedlars Edge offers a perfect blend of adventure and relaxation. This area is a favourite among skiing enthusiasts, with easy access to ski resorts and fields. The stunning views of the surrounding national parks and lakes make it a wonderful spot for hiking and sightseeing. Visitors can enjoy various outdoor activities year-round, from winter sports to summer hikes, making Pedlars Edge a versatile destination for travellers seeking both excitement and natural beauty.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to make savings on your upcoming journey? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, you could enjoy considerable discounts by opting for a longer stay. To discover a Vrbo property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a dedicated area to craft new travel plans, pick up from where you last stopped, or view and arrange your itineraries. Your previously saved and booked properties can now be easily accessed under Potential, Upcoming, or Current Trips. To explore Trip Boards, please 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)
  • Hill Top Berry Farm & Winery (3.1 mi / 4.9 km)
  • Wintergreen Resort (3.2 mi / 5.1 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 (6.5 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)
  • 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 picturesque neighbourhood offers a range of properties, from charming cabins to modern condos, suiting various preferences and budgets. Staying here places you in close proximity to the resort's top attractions, including the stunning hiking trails that wind through the Blue Ridge Mountains and the popular ski slopes during the winter months.

Another appealing aspect of this area is its access to the nearby Appalachian Trail, which is superb for outdoor enthusiasts looking to explore the natural beauty of the region. Additionally, the resort features amenities such as a golf course and spa, providing plenty of opportunities for relaxation and recreation.
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.
When is the best time to visit Wintergreen for a holiday rental?
January is the most popular time to visit Wintergreen, Virginia, as it falls within the peak season from December to February. This is when winter enthusiasts flock to the area to enjoy fantastic skiing, snowboarding, and other winter sports. With temperatures typically ranging from -5 to 5 degrees Celsius, visitors can take advantage of the crisp, invigorating climate while engaging in outdoor adventures.

During January, the slopes are in prime condition, and the resort buzzes with energy, making it an ideal time for those seeking an active holiday. The stunning views of the Blue Ridge Mountains blanketed in snow create a picturesque setting, superb for both adrenaline seekers and those looking to relax by a warm fire after a day on the slopes.

For travellers who prefer a quieter experience, May is an excellent time to consider. This month often sees fewer visitors, allowing for a more peaceful retreat. The weather begins to warm up, making it superb for hiking and enjoying the blooming flora of the region without the crowds.

Ultimately, the best time to book a holiday rental in Wintergreen depends on your preferences—whether you are drawn to the thrill of winter sports in the peak season or prefer the tranquility of spring's arrival.
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 explore a variety of attractions that cater to both nature enthusiasts and those seeking outdoor adventure. The Wintergreen Resort is a major highlight, offering a range of activities such as skiing in the winter and hiking or mountain biking during the warmer months. The resort features scenic views of the Blue Ridge Mountains, making it a superb spot for outdoor lovers.

For those interested in natural beauty, the nearby Shenandoah National Park provides stunning landscapes, with opportunities for hiking along the Appalachian Trail and enjoying breathtaking vistas at various overlooks. The park is ideal for wildlife viewing and immersing oneself in the tranquility of nature.

In addition, the local area boasts charming wineries and breweries that offer tastings and tours, allowing visitors to sample the region's best beverages while enjoying the picturesque countryside.
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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