Wintergreen Holidays
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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 Wintergreen Resort and Raven's Roost Overlook.
Top hotels in Wintergreen
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland VA
The price is €218 per night from 25 May to 26 May
€218
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (320 reviews)
Very clean, incredible view, jacuzzi tub is absolutely awesome. Remember to bring your own shampoo. Lots of hiking trails of varying difficulty close by. I hope to stay there again
Reviewed on 23 Apr 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
10/10 Exceptional! (11 reviews)
Beautiful house! Gorgeous location. Easy access to hiking trails. The host is super helpful and responsive. Highly recommend!!
Reviewed on 9 Apr 2026
Cozy Cabin with private HOT TUB!
Nellysford VA
10/10 Exceptional! (41 reviews)
We loved being able to bring our dog with us on our long weekend mountain trip. This is an older, but cozy, comfortable and unique cabin high up on a Wintergreen mountaintop, with great views of the sunset from the big bay window and especially from the wonderful hot tub. We also enjoyed making fires ...
Reviewed on 6 Apr 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.
What to do in Wintergreen
Shenandoah National Park Self-Guided Driving Audio Tour
€14
per traveller
100% of travellers recommend
Blue Ridge Parkway Self-Guided Audio Tour Bundle
€20
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
€11
per traveller
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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.
