Wintergreen Vacation Packages
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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.
Top Wintergreen Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
CA $907
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Charlottesville (CHO)
8.8/10 Excellent! (104 reviews)
The accommodations were clean but on the small side. There is no daily cleaning service in the rooms but you can request clean towels. The General Store was not well stocked. The website contains inaccurate or out of date information.
Mac's Kitchen restaurant and bar were a highlight. Both the food and the service were good.
Reviewed on Aug 8, 2026
Oakhurst Inn at the University
Jefferson Park Avenue
CA $1,649
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Charlottesville (CHO)
9.2/10 Wonderful! (593 reviews)
The first room I was in was next to some sort of mechanical room or some very loud machine sound and the floor was vibrating. The staff helped me move to a quieter room, but quiet is relative. It’s old buildings
Reviewed on Aug 11, 2026
Little Mod Hotel at the University
Venable
CA $1,666
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Charlottesville (CHO)
9.2/10 Wonderful! (360 reviews)
My best friend and I had a great stay! The staff were amazing and kind! The room was clean and loved the theme of the hotel!
Reviewed on Aug 11, 2026
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 Wintergreen Resort and Raven's Roost Overlook.
Ready to book your vacation to Wintergreen?
Wintergreen Hotel Deals
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland VA
CA $137
CA $340 total
Aug 18 - Aug 19
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 Jul 24, 2026
Endless Mountain Top Views from All The Way Up!
Wintergreen Resort VA
CA $175
CA $418 total
Aug 23 - Aug 24
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 Jul 24, 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 Aug 2, 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
Blue Ridge Parkway Self-Guided Audio Tour Bundle
CA $34
per traveller
Shenandoah National Park Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Blue Ridge Parkway Virginia Self-Guided Audio Tour
CA $18
per traveller
Frequently asked questions
How much does a Wintergreen vacation package cost?
Offering excellent value package deals from CA $907 on Expedia, you'll be thrilled with how little a vacation to Wintergreen costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Wintergreen?
March, April and August are great times to search for cheap Wintergreen vacation packages. Choosing to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Wintergreen?
Wintergreen vacations can be as short or long as you like, but to get a real feel for this destination, we'd say 3 days is a good ballpark. In this timeframe, you can fit in headline attractions like Stoney Creek Golf Course and Hill Top Berry Farm & Winery and seek out some underrated gems. Don't forget to visit neighbourhoods such as Chestnut Springs and Treeloft either. If you plan wisely, you can even allow for a day trip outside of Wintergreen too.
How to find the best Wintergreen package deals?
Use Expedia's filters to find some unbeatable Wintergreen package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Wintergreen package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Wintergreen vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a customized Wintergreen vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Wintergreen?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Wintergreen getaway.
How to plan a trip to Wintergreen?
- Choose when to get away: Check your schedule and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Wintergreen.
- Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and activities. Your accommodations will likely be the biggest expense during your trip to Wintergreen.
- Decide your trip length: Think about how much time you'd like to spend exploring Wintergreen. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the ideal Wintergreen vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
