Wintergreen Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top hotels in Wintergreen
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland VA
The price is €234 per night from 7 Jul to 8 Jul
€234
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (324 reviews)
"What a wonderful view and place to see it from. Our week was comfy and peaceful filled with adventures to delicious wineries, breweries, rides on the parkway, and a UVA baseball game. We all felt relaxed and privileged to be there. Thank you Allen. We hope to visit again.DonAugusta, GA"
Reviewed on 28 May 2026
Endless Mountain Top Views from All The Way Up!
Wintergreen Resort VA
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland VA
10/10 Exceptional! (361 reviews)
"Host was great. Nicely decorated and neat use of space. Nice wooden deck/balcony off the kitchen."
Reviewed on 24 Jun 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
€15
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
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
