Wintergreen Holidays
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Our guide on where to stay in Wintergreen
Find the best Wintergreen areas and neighborhoods for the activities you enjoy most. Learn more about Wintergreen
Chestnut Springs
While Chestnut Springs may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Raven's Roost Overlook and Wintergreen Resort.
Wintergreen Holiday
Our pick of the best Wintergreen Hotel Deals
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland VA
The price is NZ$403 per night from 8 June to 9 June
NZ$403
8 June - 9 June
includes taxes & fees
9/10 Wonderful! (323 reviews)
"Awesome views and very clean condo! We had a very relaxing weekend!"
Reviewed on 4 May 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
Wintergreen Luxury, Best Views in VA!
Wintergreen Resort VA
10/10 Exceptional! (38 reviews)
"This house was beautiful and had so much to offer. Great communication."
Reviewed on 25 May 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Wintergreen attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
