How much does a Wintergreen vacation package cost?

You'll find cheap prices from $411 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?

July, November and December are great times to look for cheap Wintergreen vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on hotels and flights.

How many days is enough for Wintergreen?

With a well-planned itinerary, you can easily tick off the main Wintergreen attractions in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Wintergreen vacation for longer.

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 when to go: Check your diary and get your bags packed. Your favorite season and the activities available will also help you decide when to escape to Wintergreen. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Wintergreen. Use our trip planning tool to discover Wintergreen: Research every part of your trip to Wintergreen with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings. Decide how long to go away for: Now that you know more about Wintergreen, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Wintergreen vacation package. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Wintergreen's best offerings. Find all the exciting things to do in Wintergreen in Wintergreen with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Wintergreen vacation packages?

Your Wintergreen getaway should be an escape from your daily routine, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

Wintergreen Vacation Packages 2026 from $411

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.

The Latest Wintergreen vacation packages

Price found within the past 48 hours. Click for updated prices.

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

$411

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

New York (LGA) to Charlottesville (CHO)

8.2/10 Very Good! (823 reviews)

The staff was lovely and so were the rooms, the lake and the horses. The restaurant serves tasty food with large portions

Reviewed on Nov 19, 2025

Oakhurst Inn at the University

Jefferson Park Avenue

$493

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

New York (LGA) to Charlottesville (CHO)

9.2/10 Wonderful! (517 reviews)

Our room was clean and the staff was super friendly and courteous. We did hope that our room had a microwave and refrigerator. It makes sense to have that available in every room on the grounds. Guests I’m sure would appreciate it. Please consider doing this. Lastly, we could here noises above us from possibly furniture that wasn’t secure. Footsteps are understandable, but the rattle of something above room 5 was a bit annoying. This is probably an eat fix. Overall the property was safe, clean and convenient.

Reviewed on Jan 1, 2026

Little Mod Hotel at the University

Venable

$483

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

New York (LGA) to Charlottesville (CHO)

9.2/10 Wonderful! (281 reviews)

Room was adorable. Very unique and comfortable experience.

Reviewed on Jan 8, 2026

The Doyle Hotel

Starr Hill

$478

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

New York (LGA) to Charlottesville (CHO)

8.6/10 Excellent! (944 reviews)

This is a beautiful hotel. Would highly recommend.

Reviewed on Jan 11, 2026

Dinsmore Boutique Inn

Venable

$493

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

New York (LGA) to Charlottesville (CHO)

9.6/10 Exceptional! (320 reviews)

Jake is always on hand for questions and assistance. Rooms are always clean.

Reviewed on Jan 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Wintergreen

View all trips

Where to stay in Wintergreen

Find the best Wintergreen areas and neighborhoods for the activities you enjoy most. Learn more about Wintergreen

Wintergreen Hotel Deals

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland VA

$215 nightly

$241 total

Jan 13 - Jan 14

Total with taxes and fees

9/10 Wonderful! (294 reviews)

Overall we had an amazing time at this location. The view was beautiful and the apartment was more than spacious enough for 4 people. The size of the kitchen was great especially when cooking big meals for everyone. We all loved having a wood fireplace and being able to enjoy the warmth and hearing ...

Reviewed on Dec 14, 2025

The Modern Mountain Condo

Wintergreen Resort VA

$210 nightly

$236 total

Jan 13 - Jan 14

Total with taxes and fees

9.8/10 Exceptional! (37 reviews)

Beautiful home that made the perfect mountain ski weekend. The host was great at communicating and made our trip wonderful and stress free!

Reviewed on Dec 27, 2025

Lofty Pursuits: Spectacular View + EV Charger

Wintergreen Resort VA

$368 nightly

$392 total

Jan 13 - Jan 14

Total with taxes and fees

10/10 Exceptional! (5 reviews)

From the moment we entered “Lofty Pursuits,” we knew we had reserved just the right place for our mini-vacation. The views, furnishings, cleanliness, and location were perfect. We came to relax, not ski, and we loved our five days. In summary, this was a truly cozy place to stay!One thing to note: ...

Reviewed on Dec 26, 2025

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.

Things to do near Wintergreen

Wintergreen offers an exciting blend of outdoor adventures and sports, making it a perfect vacation spot. Visitors can enjoy skiing on the ski fields, take scenic chairlift rides, or engage in mountain biking. For family-friendly fun, mini golf and disc golf are available. Don't forget to make activity reservations at the resort to fully experience all that Wintergreen has to offer.

Shopping

In Wintergreen, you can shop at local boutiques and gift shops for unique souvenirs. If you're up for a drive, Windmill Square is 13 miles away, offering a variety of shops. Staunton Mall and Orchard Hill Square Shopping Center, both 19 miles away, provide a wider selection for your shopping needs.

Recreation

At Stoney Creek Golf Course, enjoy a round of golf surrounded by scenic landscapes and outdoor vibes, located 1 mile from Wintergreen. For relaxation, head to Sherando Lake Recreation Area, 7 miles away, where you can unwind amidst nature's tranquility. Experience culture and entertainment at Wayne Theatre, 13 miles from Wintergreen.

Adventure

At Wintergreen Resort, enjoy skiing on pristine slopes with breathtaking views, just 3 miles from Wintergreen. For hiking enthusiasts, the Reids Gap Trailhead offers scenic trails and outdoor adventure, located 5 miles away. Don't miss a visit to Caromont Farm, 15 miles away, for a unique farm experience.

Nightlife

Wintergreen offers a cozy nightlife with venues like The Edge Restaurant & Lounge, perfect for a relaxed dinner and drinks. For live music and entertainment, check out the nearby Wintergreen Resort. Enjoy the stunning mountain views while sipping cocktails and socializing with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Wintergreen

Wintergreen, Virginia, is an ideal destination for ski enthusiasts and adventure seekers. Explore a variety of attractions, including ski resorts, museums, and historic houses that offer a blend of culture and outdoor experiences. Whether you’re hitting the slopes or delving into local history, Wintergreen provides plenty of activities for every traveler. Don't miss out on the unique wintergreen attractions that enhance your visit to this charming area.

Wintergreen Resort: Experience the thrill of skiing at Wintergreen Resort, a premier destination just 3 miles away. With its stunning slopes and outdoor adventure vibes, this resort promises fun for all skill levels, making it perfect for families and thrill-seekers alike.
Blue Ridge Parkway North Entrance: Located 10 miles away, this visitor center welcomes you with outdoor adventure and family-friendly activities. Enjoy breathtaking views and learn about the natural beauty of the Blue Ridge Mountains while soaking up the area's rich history.
Raven's Roost Overlook: A scenic lookout just 4 miles from Wintergreen, Raven's Roost Overlook offers romantic vistas and adventure vibes. It's an ideal spot for couples to share a moment while taking in the stunning panoramic views of the surrounding landscape.

Best time to go to Wintergreen

The best time to visit Wintergreen is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	33.4°F (0.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly Low
February	37.2°F (2.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly Low
March	44.6°F (7.0°C)	Light Rain	Mostly Sunny	Average	Average
April	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Average
May	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly High
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Moderately Low	Average
July	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Average	Average
August	74.3°F (23.5°C)	Light Rain	Mostly Sunny	Moderately Low	Average
September	68.0°F (20.0°C)	Light Rain	Mostly Sunny	Average	Average
October	56.8°F (13.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	44.8°F (7.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
December	38.5°F (3.6°C)	Light Rain	Mostly Sunny	Moderately High	Slightly Low

Tips to save on your trip to Wintergreen

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Wintergreen.
Consider traveling to Wintergreen during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language	English
Currency	U.S dollars
Closest Airport	Charlottesville-Albemarle Airport (CHO)
Population	170
Max Temp Winter	45ºF
Max Temp Summer	85ºF
Top Sights	Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course

Language

English

Currency

U.S dollars

Closest Airport

Charlottesville-Albemarle Airport (CHO)

Population

170

Max Temp Winter

45ºF

Max Temp Summer

85ºF