Photo by Rebecca Brent

Wintergreen chalet rentals

We found 16 chalet rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any chalets in Wintergreen?
Stay in one of our 16 chalets in Wintergreen and you'll have a perfect base for your next outdoor adventure. Pedlars Edge, Treeloft and Laurel Ridge are some of the city's most popular areas to stay.
How much does it cost to stay in a chalet in Wintergreen?
Prices vary depending on length of stay, season and exact location, so key in your trip details to check out what's available in Wintergreen. Whether you're dreaming of a traditional wooden chalet with rustic appeal or a sleek, modern one boasting all the bells and whistles, we'll help you find a holiday property within your price range.
When is the best time to rent a chalet in Wintergreen?
Marvel at the beauty of nature as you enjoy the comforts and conveniences of a cosy chalet in June. This is the ideal time for many people to book one of our chalets in Wintergreen, with the average temperature ranging from 16ºC to 28ºC. If you want help deciding the perfect time to organise a visit to Nellysford, have a look at some tourism websites or travel guides.
Where can I rent a Wintergreen chalet with great views?
Stayz makes it easy to find the stunning views you're looking for in your holiday property. You can use the "Location" filter to narrow down the type of area you'd prefer to stay in, and the views you like to stare out at, while browsing chalets in Wintergreen.
Can I book a luxury chalet in Wintergreen?
Exuding style and nestled among gorgeous landscapes, our upmarket Wintergreen chalets promise an unforgettable holiday experience. With amenities like hot tubs, state-of-the-art kitchen appliances and sprawling living spaces, Stayz chalets are perfect for unwinding after a day of exploration.
Are there any catered chalets in Wintergreen?
There's no need to waste precious holiday time cooking and grocery shopping when you opt for a Wintergreen catered chalet. Experienced chefs and hosts will ensure tasty meals are served every day, giving you more time to relax and recharge during your break. What's more, they'll even prepare snacks and picnics for you to enjoy.
What are the top things to do in Wintergreen?
It's easy to see why many families love Wintergreen, with popular attractions like Crabtree Falls, Stoney Creek Golf Course and Sherando Lake Recreation Area to explore. Discover this destination's wonders together and then return to the cosy comforts of your chalet.
Why should I book my chalet holiday rental with Stayz?
Stayz takes the stress out of booking your next chalet break. Use our filter tool to narrow down your search for the perfect space by location, amenities and more. One of the best things about us? We offer chalets that go beyond the regular hotel room — think private lakefront pads and ski-in rental options. Need to change plans? Check out our cancellation policies to see if you're eligible for a complete refund.