Wintergreen holiday rentals

We found 931 holiday rentals — enter your dates for availability
Select from 225 houses, 316 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:30 Oct - 6 Nov

Image gallery for Three Ridges Haven- Devils Backbone Brewing Company

Interior
9.4 out of 10, Exceptional, (82 reviews)
Exceptional
(82 reviews)

Three Ridges Haven- Devils Backbone Brewing Company

Roseland

25% off
Price is AU$6,880
for 7 nights, 1 room
AU$983 per night
includes taxes & fees
Three Ridges Haven- Devils Backbone Brewing Company

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Wintergreen

  • Adventurous skiing and outdoor pursuits: Wintergreen offers thrilling ski slopes and a host of adventure sports set against the majestic Blue Ridge Mountains.
  • Stunning natural landscapes: Revel in the breathtaking valley views and explore the surrounding national and state parks.
  • Cultural attractions: Discover local history through museums and historic houses that capture the charm of the area.
  • Family-friendly excursions: Enjoy a variety of recreational activities suitable for visitors of all ages.
  • Tranquil holiday living: Embrace a peaceful retreat with cosy and comfortable accommodation options in a picturesque setting.

Popular types of accommodation in Wintergreen

Welcome to Wintergreen, Virginia, where scenic beauty meets tranquil holiday living. Renowned for its Private Holiday Homes, Condos and Cabins, Wintergreen offers a variety of accommodation options including wintergreen homesites, wintergreen va homes, next home at wintergreen resort, holiday home, and homes within wintergreen resort. Explore local attractions, enjoy breathtaking landscapes, and experience the charm of this picturesque city.

  • Private Holiday Homes: A favourite choice for visitors, these spacious residences offer a home-like experience with all the comforts you need for a delightful stay.
  • Condos: Ideal for those seeking modern amenities, condos provide a blend of comfort and convenience in a vibrant community setting.
  • Cabins: Embrace nature in these charming retreats, perfect for a cosy getaway surrounded by the beautiful Virginia landscape.
  • Apartments: Offering a practical and central option, apartments are great for short stays while enjoying easy access to local attractions.
  • Cottages: Quaint and often tucked away, cottages provide a peaceful escape, perfect for a romantic getaway or family retreat.**

Top attractions near Wintergreen

Wintergreen, Virginia, is a charming destination perfect for skiing and adventure sports enthusiasts. Visitors can explore a variety of attractions, including museums and historic houses, as well as the stunning landscapes of nearby national and state parks. Whether seeking cultural experiences or outdoor adventures, Wintergreen offers a delightful blend of activities that cater to all interests, making it an ideal spot for a memorable holiday.

  • Walton's Mountain Museum: Located 21km from Wintergreen, this museum offers a rich cultural experience, displaying local artefacts and historical narratives that capture the spirit of the region.
  • Oak Ridge Estate: Situated 19km away, this historic house exudes cultural heritage with its well-preserved architecture and period furnishings, offering a glimpse into the past.
  • Rockfish Gap Entrance Shenandoah: Positioned 18km from Wintergreen, this national state park invites outdoor enthusiasts to explore scenic landscapes and partake in adventurous pursuits.

Things to do recommended for couples

Wintergreen offers a magical retreat 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 a romantic stargazing session; the clear night skies provide a perfect backdrop for love.

Things to do recommended for families

Families visiting Wintergreen can enjoy skiing or snowboarding at the local slopes, take scenic hikes through the Blue Ridge Mountains, and explore the fun-filled activities at the Wintergreen Nature Foundation, offering educational programs for children of all ages.

Things to do recommended for groups

Explore the stunning Blue Ridge Mountains with a group hike along the Appalachian Trail or enjoy a day of skiing at Wintergreen Resort. For a unique experience, consider a guided wine tour of local vineyards, perfect for tasting Virginia's finest offerings together.

*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 if you’re seeking longer stays, it’s important to use the appropriate filters to match your priorities. Here are some helpful Stayz booking tips for you.

  • Traveling to Wintergreen with a group: Consider how many bedrooms you will require, along with facilities like a fully equipped kitchen or an outdoor area for social gatherings. Thankfully, on Stayz, you can refine your search to include all these options and many others.
  • Traveling to Wintergreen with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, such as 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 holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Stayz accommodations that welcome pets. The majority of pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you're seeking holiday lets offering special rates for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly find and secure savings on monthly rentals. You may also want to consider including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Wintergreen

Wintergreen, Virginia, is a delightful village perfect for an adventurous holiday. Nestled among the stunning Blue Ridge Mountains, it offers thrilling skiing and outdoor activities for nature lovers. Enjoy family-friendly excursions and recreational opportunities, all while soaking in the breathtaking valley views. Whether you seek a winter getaway or a peaceful retreat, Wintergreen provides a unique blend of relaxation and excitement, making it an ideal destination for all types of travellers.

  • Nellysford: Nestled in the heart of Virginia, Nellysford is a charming city that serves as the gateway to Wintergreen. Renowned for its exhilarating skiing and adventure sports, this area attracts outdoor enthusiasts year-round. Visitors can indulge in a variety of activities such as skiing on well-maintained slopes at nearby ski resorts. The scenic surroundings boast stunning natural landmarks, including the expansive national state park and picturesque lakes, making it an ideal spot for both relaxation and exploration.
  • Chestnut Springs: Located closely to Wintergreen, Chestnut Springs is a delightful neighbourhood known for its adventurous spirit. It offers a similar allure to its neighbouring city, drawing visitors keen on skiing and outdoor sports. The area is surrounded by breathtaking landscapes, including lakes and national parks, which provide ample opportunities for hiking and nature walks. Chestnut Springs is a perfect base for travellers looking to immerse themselves in the local natural beauty while enjoying a variety of recreational activities.
  • Three Ridges Wilderness: Just a short drive from Wintergreen, Three Ridges Wilderness is a stunning natural park that beckons those seeking adventure and captivating scenery. This wilderness area is characterised by dramatic landscapes, dense forests, and panoramic views, making it a haven for hikers and outdoor enthusiasts. Popular activities here include skiing and exploring the nearby national state park and nature reserves. Whether you’re trekking through the forests or simply soaking in the tranquil environment, Three Ridges Wilderness promises an unforgettable experience 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.

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 Stayz is a breeze

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you might enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a convenient area for you to craft new journeys, carry on with your plans, or review and manage your bookings. The properties you've either saved or reserved are now organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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:

  • Hill Top Berry Farm & Winery (3.1 mi / 4.9 km)
  • Wintergreen Resort (3.2 mi / 5.1 km)
  • Cardinal Point Vineyard and Winery (8.5 mi / 13.7 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 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:

  • Humpback Rocks (5.3 mi / 8.5 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)
  • Reids Gap Trailhead (4.8 mi / 7.8 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 home?
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 home accommodation in Wintergreen?
Condos are the most popular type of holiday home in Wintergreen, according to our data. Even if you've got a different vision in mind, Stayz 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 home in Wintergreen?
Different factors affect how much you'll pay for a holiday home 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 home 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 Stayz 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 homes 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 homes on Stayz. 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 Stayz. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your Stayz holiday home has its own swimming pool.
What are popular home amenities in Wintergreen?
Some of the most popular home 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, Stayz holiday properties have the best amenities for beginning new traditions with the people you cherish the most.
Are there large group holiday homes 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 homes 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 homes in Wintergreen?
Wintergreen has 65 one-bedroom homes 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 homes in Wintergreen?
Pick from 82 two-bedroom holiday homes 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 homes with WiFi in Wintergreen?
Wintergreen has 149 holiday homes 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 Stayz homes make it a cinch to get online.
How can I find holiday homes with air conditioning in Wintergreen?
Decide on your travel dates and then use the filters to look for holiday homes with ac in Wintergreen on Stayz. 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 home in Wintergreen?
It's a good idea to check with the Wintergreen holiday home you're looking at on Stayz as the minimum age differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday home 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 Stayz 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.