Wintergreen Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 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 Wintergreen Resort and Raven's Roost Overlook.
Top hotels in Wintergreen
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
10/10 Exceptional! (10 reviews)
We had a great experience! The host was extremely responsive and the house was amazing. We loved the hot tub, the views and that the house had everything we needed plus more. We even had an issue on my end that we had to very last minute add a pet that they were understanding about. Would definitely ...
Reviewed on 1 Mar 2026
The Modern Mountain Condo
Wintergreen Resort VA
The price is €201 per night from 26 Mar to 27 Mar
€201
26 Mar - 27 Mar
includes taxes & fees
10/10 Exceptional! (46 reviews)
The property was just as described and the communication was a breeze. The view from the unit’s deck was beautiful.
Reviewed on 17 Mar 2026
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland VA
10/10 Exceptional! (349 reviews)
We had a wonderful time! The condo was perfect for our family of 4 with 2 small dogs. The condo was clean, well laid out, and very well stocked. It had everything we needed and more! The communication with the host was super fast and helpful. We already booked for next year!
Reviewed on 15 Mar 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
Blue Ridge Parkway Self-Guided Audio Tour Bundle
€21
per traveller
Shenandoah National Park Self-Guided Driving Audio Tour
€15
per traveller
100% of travellers recommend
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.
