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 Wintergreen Resort and Raven's Roost Overlook.
Treeloft
Though Treeloft may not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook.
Pedlars Edge
1 out of top 10 points of interest in this area
While Pedlars Edge isn't home to many top sights, Wintergreen Resort and Raven's Roost Overlook are some notable places to visit nearby.
Laurel Ridge
Laurel Ridge might not have many top sights, but Wintergreen Resort and Reids Gap Trailhead are two attractions nearby that you can check out.
Deer Springs
Though Deer Springs may not have many top sights, you can venture to the surrounding area to see attractions 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
€218
18 Aug - 19 Aug
includes taxes & fees
9/10 Wonderful! (329 reviews)
"The stay was pleasant. The location is very nice with a great view but the condo is starting to show some age so a few renovations and updates are needed."
Reviewed on 24 Jul 2026
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland VA
10/10 Exceptional! (368 reviews)
"Beautiful condo close to the Mountain Inn. Kitchen is well stocked and the owners provide a lot for your furry companions. We had a great time hiking the trails and coming back for a quiet evening. Wonderful place to stay and I can't wait to come back!!"
Reviewed on 2 Aug 2026
Endless Mountain Top Views from All The Way Up!
Wintergreen Resort VA
€230
10 Aug - 11 Aug
includes taxes & fees
10/10 Exceptional! (117 reviews)
"Great location with amazing views, perfect size living space, and everything we needed. Easy access to walking, hicking, swimming, golf, spa, food, etc. Short drive to wineries, recreational lake and local restaurants. Really didn't have to leave the mountain for much. Super enjoyable ..."
Reviewed on 24 Jul 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
Wintergreen Resort
8.8/10 (140 reviews)
Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.
Photo by Brittany Davidson
Raven's Roost Overlook
Find out about the history of Wintergreen with a stop at Raven's Roost Overlook. Discover the mountain views and top-notch restaurants in this vibrant area.
Bold Rock Hard Cider Nellysford Cidery
9.4/10 (21 reviews)
You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Wintergreen. Discover the mountain views in this family-friendly area or seek out the ski slopes.
Stoney Creek Golf Course
10.0/10 (3 reviews)
Enjoy a round of golf in Wintergreen at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.
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
€21
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
€11
per traveller
Frequently asked questions
How much does a Wintergreen holiday package cost?
You'll find cheap prices on Expedia for your Wintergreen break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Wintergreen costs.
What are the cheapest months to go to Wintergreen?
If you'd like to score a cheap Wintergreen holiday package, consider travelling in March, April and August. You'll generally find better rates on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Wintergreen?
The ideal duration of your Wintergreen holiday depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to check out all the top sights and explore some hidden gems along the way.
How to find the best Wintergreen package deals?
Begin your search for a Wintergreen package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Wintergreen package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Wintergreen adventure off to a flying start.
Is it cheaper to book a Wintergreen holiday as a package?
You can enjoy significant savings on your next Wintergreen break by booking a customised holiday package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Wintergreen?
If you've got your Wintergreen travel dates locked in, book early to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Wintergreen?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Wintergreen.
- Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Wintergreen.
- Decide how long to go for: Now that you're more familiar with Wintergreen, you can figure out the ideal length of your holiday. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Wintergreen holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
