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Wintergreen vacation rentals

We found 892 vacation rentals — enter your dates for availability

Select from 231 houses, 311 condos, and other vacation rentals to find the perfect place for your stay in Wintergreen. Vacation homes offer the amenities you expect for your family, friends, or furry companion, such as a garden and pool. At the end of the day, you're sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Wintergreen

Showing deals for:Mar 20 - Mar 27

Image gallery for Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing

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

Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing

Roseland

10% off
Price is CA $540
CA $4,971 total
includes taxes & fees
Pet Friendly with Mountain views ON 151 BrewRidge Trl near Wineries~Hikes~Skiing

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Find out more about Wintergreen

Why visit Wintergreen

  • Exceptional skiing: Wintergreen is renowned for its ski resorts, offering thrilling slopes and family-friendly options.
  • Breathtaking mountain views: Experience stunning vistas and natural beauty throughout the region, perfect for outdoor lovers.
  • Pleasant accommodations: Choose from charming vacation rentals, including cozy condos and rustic cabins for a memorable stay.
  • Variety of activities: Engage in diverse outdoor pursuits, from golfing to hiking, ensuring fun for all ages.
  • Culinary delights: Savor local cuisine at delightful restaurants that enhance your Wintergreen experience.

Popular types of accommodation in Wintergreen

Planning a getaway to Wintergreen? You’re in for a treat. Discover the charm of Wintergreen vacation rentals, including houses, cozy condos, and rustic cabins. Whether you're hitting the slopes at Wintergreen Resort or exploring the stunning outdoors, our selection of Wintergreen resort vacation rentals ensures you'll find the perfect home base for your adventure. Embrace the comfort and convenience of Wintergreen condos to make your stay memorable.

  • Houses: The top choice for visitors, these spacious homes offer the comforts of home, perfect for families or groups seeking a memorable getaway in Wintergreen.
  • Condos: A popular option for those who prefer modern amenities and convenient locations, ideal for couples or small families.
  • Cabins: Experience the charm of rustic living in cozy cabins surrounded by nature, perfect for a serene retreat.
  • Apartments: Comfortable and practical, these rentals provide a home-like atmosphere for solo travellers or couples.
  • Cottages: Quaint and inviting, cottages offer a delightful escape, combining charm with a touch of wilderness.**

Top attractions near Wintergreen

Wintergreen, Virginia, is the perfect destination for adventure and sports enthusiasts, especially those keen on skiing. Visitors can explore a variety of attractions including ski resorts, museums, and historic houses. Whether you're seeking outdoor thrills or cultural experiences, Wintergreen offers something for everyone. Don't miss the chance to enjoy the Wintergreen ski area, dine at local restaurants, and discover family-friendly ski resorts in the area for an unforgettable vacation.

  • Wintergreen Resort: Nestled 4.8km from Wintergreen, this ski resort offers thrilling winter sports and outdoor adventures. With its stunning slopes and vibrant atmosphere, it's perfect for both skiing enthusiasts and families seeking fun in the snow.
  • Blue Ridge Parkway North Entrance: Located 16.1km away, this visitor centre is a gateway to breathtaking scenery and outdoor activities. It's an ideal spot for families to explore nature and embark on memorable adventures.
  • Raven's Roost Overlook: Just 6.4km from Wintergreen, this picturesque lookout provides romantic views and outdoor excitement. It's a fantastic place for couples to enjoy the beauty of the Blue Ridge Mountains together.

Things to do recommended for couples

Planning a couple's getaway in Wintergreen? Enjoy skiing at Wintergreen Resort, just 4.8km away, or indulge in wine tasting at Hill Top Berry Farm & Winery, also 4.8km away. For a special experience, visit Veritas Vineyard and Winery, located 16.1km from Wintergreen.

Things to do recommended for families

Families will love the serene Sherando Lake Recreation Area, located 11.3km from Wintergreen. This beautiful spot offers wellness and relaxation vibes, perfect for picnics, hiking, and enjoying nature together.

Things to do recommended for groups

Experience the charm of Bold Rock Hard Cider for a refreshing drink, challenge your friends at Stoney Creek Golf Course, or embark on an adventure together at Reids Gap Trailhead for stunning scenery. Wintergreen offers the perfect blend of relaxation and outdoor fun for your group getaway.

*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 planning a trip with friends, family, pets, or considering extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, and to look for amenities that suit their age, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make your trip even more enjoyable.
  • Taking your pets with you to Wintergreen: For many families, a vacation isn't truly fulfilling without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you’re in search of vacation rentals offering 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 rental options. Don’t forget to include features like a parking spot, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Wintergreen

Wintergreen, Virginia, is a fantastic destination for outdoor enthusiasts seeking ski adventures and breathtaking mountain views. During your visit, explore the picturesque golf courses and enjoy family-friendly activities in the scenic outdoor areas. This winter getaway offers a perfect blend of relaxation and recreation, allowing you to immerse yourself in both the vibrant atmosphere of the village and the serene beauty of the surrounding region.

  • Nellysford: Nellysford is a charming city that serves as the gateway to Wintergreen, offering an exciting blend of outdoor adventure and picturesque landscapes. Known for its skiing opportunities, Nellysford attracts visitors seeking thrilling experiences on the slopes. Nearby ski resorts and fields provide ample chances for skiing and snowboarding. Additionally, the area is home to stunning local landmarks, including serene lakes and the expansive national state park, making it ideal for both winter sports enthusiasts and nature lovers. Whether you're hitting the slopes or exploring the natural beauty, Nellysford promises an unforgettable experience.
  • Pedlars Edge: Nestled around Wintergreen, Pedlars Edge is a vibrant neighbourhood that shares the thrill of outdoor adventures. Visitors flock to this area for its outstanding skiing facilities, with accessible ski fields and resorts catering to all levels. The breathtaking surroundings include nearby lakes and a national park, providing a perfect backdrop for activities like hiking and wildlife viewing during the off-peak season. Pedlars Edge is a fantastic choice for those looking to immerse themselves in the beauty of Virginia while enjoying a variety of sports and recreational opportunities.
  • Chestnut Springs: Located a mere 6.4km from Wintergreen, Chestnut Springs is an inviting neighbourhood that attracts adventure seekers and sports enthusiasts alike. Visitors can indulge in skiing experiences at the nearby resorts and enjoy the thrill of the ski fields. The area is enriched by local attractions such as tranquil lakes and the expansive national state park, offering a perfect escape into nature. Whether it's skiing in winter or exploring scenic trails in warmer months, Chestnut Springs provides a rich tapestry of experiences for every type of traveller.

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 simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can help, as prices can vary quite a bit. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your itinerary, or review your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Why people love visiting beautiful Wintergreen

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

Activities and attractions in and around Wintergreen

Do you want to discover attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Wintergreen has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • 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)

Exploring the natural landscape of Wintergreen

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Wintergreen is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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

Travelers 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 1 inches and temperatures average 38°F.

Traveling 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 center. If you can't find a flight that works for your travel itinerary, you can also fly into Charlottesville-Albemarle Airport (CHO), which is 30.3 mi (48.8 km) away.

Frequently asked questions

What is the best area to stay in Wintergreen when booking a vacation rental?
When considering a vacation rental in Wintergreen, Virginia, a popular area to stay is near the Wintergreen Resort. This neighbourhood offers a lot of rental properties, suiting a variety of tastes and budgets. Staying here places you right in the heart of the action, with immediate access to the resort's ski slopes and hiking trails, making it ideal for both winter sports enthusiasts and summer adventurers alike.

Another appealing option is the area around Lake Monocan, which provides a serene setting for those looking to relax. This neighbourhood features a range of properties, many of which offer stunning views of the lake and surrounding mountains. The lake itself is a fantastic spot for swimming, fishing, and kayaking, creating a great recreational escape.
How much does it cost to rent a vacation home in Wintergreen?
Prices for vacation 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 travelling 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.
Are there any discounts for Wintergreen vacation 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 vacation rentals in Wintergreen?
A long-stay vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The best time to visit Wintergreen for a vacation rental is from December to February, with January being the most popular month. During this peak season, winter sports enthusiasts flock to the area, eager to hit the ski slopes and enjoy a range of outdoor activities. With a variety of ski trails and pristine snow conditions, Wintergreen transforms into a winter wonderland, offering both exhilarating skiing and relaxing après-ski experiences.

January typically sees average temperatures hovering around -1°C to 3°C, creating a crisp yet enjoyable atmosphere for outdoor adventures. This month is particularly ideal for those who love winter sports, as the resort is fully operational, and you can easily access well-groomed trails.

If you're looking for a quieter experience and more affordable vacation rentals, consider visiting in May. The transition into spring brings blooming wildflowers and picturesque landscapes, great for hiking and enjoying the natural beauty without the hustle and bustle of peak winter traffic.
How early should I book a Wintergreen vacation rental?
Book your Wintergreen vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Wintergreen home rental booking on Vrbo?
To find Wintergreen vacation 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 vacation 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.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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