We found 911 holiday rentals — enter your dates for availability
Select from 232 houses, 315 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:29 Jan - 5 Feb
Image gallery for Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
1010 out of 10, Exceptional, (85 reviews)
Exceptional
(85 reviews)
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
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Enjoy full kitchens, laundry, pools, gardens and more
More for less
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Find out more about Wintergreen
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 Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
33.4°F (0.8°C)
Light Rain
Mostly Sunny
Moderately High
Slightly High
February
37.2°F (2.9°C)
Light Rain
Mostly Sunny
Moderately High
Slightly High
March
44.6°F (7.0°C)
Light Rain
Mostly Sunny
Average
Slightly Low
April
54.9°F (12.7°C)
Light Rain
Mostly Sunny
Average
Slightly Low
May
64.0°F (17.8°C)
Light Rain
Mostly Sunny
Moderately Low
Average
June
72.1°F (22.3°C)
Light Rain
Mostly Sunny
Moderately Low
Average
July
76.6°F (24.8°C)
Light Rain
Mostly Sunny
Average
Slightly Low
August
74.3°F (23.5°C)
Light Rain
Mostly Sunny
Moderately Low
Average
September
68.0°F (20.0°C)
Light Rain
Mostly Sunny
Average
Average
October
56.8°F (13.8°C)
Light Rain
Mostly Sunny
Average
Average
November
44.8°F (7.1°C)
Light Rain
Mostly Sunny
Average
Average
December
38.5°F (3.6°C)
Light Rain
Mostly Sunny
Moderately High
Slightly 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.
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.
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.
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.
Are all fees included in the Wintergreen holiday homes prices shown on Stayz?
Stayz 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.
Are there any Wintergreen holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Wintergreen holiday homes?
You can find great discounts on holiday homes in Wintergreen on Stayz, 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 change or cancel my Wintergreen holiday home booking on Stayz?
To find Wintergreen holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wintergreen?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Wintergreen holiday home?
Book your Wintergreen holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wintergreen?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Wintergreen to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way.
Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.