Wintergreen Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook.
Treeloft
When in Treeloft, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.
Pedlars Edge
1 out of top 10 points of interest in this area
If you're looking for some top things to see and do in Pedlars Edge and surrounding area, you can visit Wintergreen Resort and Raven's Roost Overlook.
Laurel Ridge
When in Laurel Ridge, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.
Deer Springs
If you're looking for some top things to see and do in Deer Springs and surrounding area, you can visit Raven's Roost Overlook and Wintergreen Resort.
Find the Best Wintergreen Vacation Packages
Wintergreen Hotel Deals
Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort VA
￥17,995
￥43,785 total
Oct 6 - Oct 7
includes taxes & fees
9.8/10 Exceptional! (38 reviews)
"This well-equipped condo was central to the market and restaurants. We enjoyed the fireplace and the deck."
Reviewed on Sep 29, 2026
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland VA
10/10 Exceptional! (374 reviews)
"Wonderful condo in a good location with pretty easy walking access to the main lodge and market store. We really enjoyed this property."
Reviewed on Sep 2, 2026
Cozy Cabin with private HOT TUB!
Nellysford VA
10/10 Exceptional! (50 reviews)
"Nice house/property. Excellent location for nature/breweries."
Reviewed on Sep 5, 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 when you take a trip to 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
￥2,665
per traveler
100% of travellers recommend
Blue Ridge Parkway Self-Guided Audio Tour Bundle
￥3,764
per traveler
Blue Ridge Parkway Virginia Self-Guided Audio Tour
￥2,038
per traveler
Frequently asked questions
How much does a Wintergreen vacation 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 vacation to Wintergreen costs.
What are the cheapest months to go to Wintergreen?
If you'd like to score a cheap Wintergreen vacation package, consider traveling in March, April and August. You'll generally find better rates on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Wintergreen?
The ideal duration of your Wintergreen vacation 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 vacation as a package?
You can enjoy significant savings on your next Wintergreen break by booking a customized vacation 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 vacation 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 vacation. 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 vacation 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.
