
Wintergreen Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Wintergreen Vacation
When a break in the city is calling, answer it with a Wintergreen vacation package. The neighborhood of Laurel Ridge, which is good for skiing, adventure sports and mountain biking, makes a fantastic base for your adventures. Fill your days with visits to Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course and Hill Top Berry Farm & Winery, some of the things you simply have to see during a trip to Wintergreen. Don't delay exploring this city any longer. Your dream Wintergreen vacation is only a few clicks away with Expedia.
Where to stay in Wintergreen

Chestnut Springs
Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Raven's Roost Overlook and Wintergreen Resort.
Wintergreen Hotel Deals

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
"I didn't have a good experience here. Some things I could have dealt with, like the hot tub was unreasonably loud, and there was a Keurig but no coffee. However, I had two major issues. One is that the back wall is entirely floor to ceiling windows, but only half of the windows had functional curtains. ..."
Reviewed on Jun 11, 2026

Endless Mountain Top Views from All The Way Up!

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
"Host was great. Nicely decorated and neat use of space. Nice wooden deck/balcony off the kitchen."
Reviewed on Jun 24, 2026
Stay near popular Wintergreen attractions
What to do in Wintergreen

Blue Ridge Parkway Self-Guided Audio Tour Bundle

Shenandoah National Park Self-Guided Driving Audio Tour











