How much does a Wintergreen vacation package cost?

You'll find cheap prices from $498 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 2025/2026 from $252

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.

Mayhurst Inn

$498

per person

Sep 25 - Sep 27

found 6 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Charlottesville (CHO)

9.2/10 Wonderful! (281 reviews)

I don’t think we've stayed in a more unique, interesting, and truly relaxing setting in our 56 yrs of marriage! The host was marvelous and the home and grounds were history come alive. The entire family was brimming with energy. Strongly recommended. You won't be disappointed!

Reviewed on Aug 20, 2025

Dinsmore Boutique Inn

Venable

$841

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Burlington (BTV) to Charlottesville (CHO)

9.6/10 Exceptional! (288 reviews)

We thoroughly enjoyed our stay at the Dinsmore. Its location, ease of access, and the friendly staff helped make our stay perfect! Jake was so helpful and kind. The adjacent Farm Bell Restaurant exceeded all expectations.

Reviewed on Aug 19, 2025

Little Mod Hotel at the University

Venable

$760

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Burlington (BTV) to Charlottesville (CHO)

9.2/10 Wonderful! (241 reviews)

Very nicely decorated in a 1960's style.

Reviewed on Aug 19, 2025

Oakhurst Inn at the University

Jefferson Park Avenue

$832

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Burlington (BTV) to Charlottesville (CHO)

9.2/10 Wonderful! (480 reviews)

The property was nice and not too far from UVA and downtown area

Reviewed on Aug 10, 2025

Oasis Near Charlottesville With Pool Grill

$2,523

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Burlington (BTV) to Charlottesville (CHO)

No reviews

Don't see what you're looking for?

See all available trips from San Antonio to Wintergreen

View all trips

Wintergreen Hotel Deals

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland

10/10 Exceptional! (320 reviews)

"Very comfortable with considerate hosts. Easy walking distance to resort. Highly recommend!"

Reviewed on Jul 27, 2025

Get rates

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Nellysford

$378 nightly

$425 total

Aug 25 - Aug 26

Total with taxes and fees

9.8/10 Exceptional! (19 reviews)

Perfect location

"We had such a great girls weekend!! The Cottage was so cute, fun, clean and beds were super comfy. The house was in the perfect location for everything. Can’t wait to go back."

Reviewed on Mar 10, 2025

Hotel 24 South

24 South Market Street, Staunton, VA

Fully refundableReserve now, pay when you stay

$114 nightly

$128 total

Sep 7 - Sep 8

Total with taxes and fees

9.4/10 Exceptional! (1,000 reviews)

"We were greated by a warm staff which is always nice. However, there was a boil notice in place which did affect our stay. Not the hotel's fault but offering guests a single bottle of water was not a sufficient response. Barring the water issue it was a pleasant stay."

Reviewed on Aug 17, 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, Virginia, is an ideal destination for ski and adventure enthusiasts, offering a variety of activities such as skiing at its popular ski resort, chairlift rides, mountain biking, and fun games like mini golf and disc golf. Visitors can also make activity reservations at the resort to ensure a memorable experience filled with outdoor excitement.

Shopping

In Wintergreen, you can shop at Windmill Square, a cozy shopping center that captures a family-friendly vibe. If you're up for a drive, check out Staunton Mall and Orchard Hill Square Shopping Center, both offering a mix of shops with a vibrant city atmosphere.

Recreation

At Stoney Creek Golf Course, enjoy a round of golf surrounded by scenic landscapes just a mile from Wintergreen. For relaxation, visit Sherando Lake Recreation Area, seven miles away, where you can unwind amidst nature. Experience culture and entertainment at the Wayne Theatre, located 13 miles from Wintergreen.

Adventure

Wintergreen Resort is an exhilarating ski destination located 3 miles from Wintergreen, offering skiing and outdoor adventures amid scenic mountain views. For hiking enthusiasts, Reids Gap Trailhead, situated 5 miles away, presents breathtaking scenery along its trails. Don’t miss Caromont Farm, located 15 miles away, for a unique local experience.

Nightlife

Experience Wintergreen's nightlife at The Edge Restaurant and Lounge, where après-ski vibes meet live music. Enjoy craft cocktails and local brews at the nearby Devils Backbone Brewing Company, known for its lively atmosphere and outdoor seating. For a cozy evening, visit the Wintergreen Resort for seasonal events and entertainment.

*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 perfect for ski and adventure enthusiasts, offering a range of attractions like ski resorts, museums, and historic houses. Whether you're seeking cultural experiences or outdoor adventures, Wintergreen has something for everyone. Don't miss out on the local attractions that showcase the area's natural beauty and rich history, making your visit an unforgettable experience.

Wintergreen Resort: Experience the thrill of skiing and snowboarding at Wintergreen Resort, just 3 miles away. This premier ski resort offers a range of winter sports, adventure activities, and breathtaking outdoor scenery, making it perfect for both adrenaline seekers and families looking to enjoy the slopes.
Blue Ridge Parkway North Entrance: Located 10 miles away, this visitor center is the gateway to outdoor exploration. With stunning views and family-friendly activities, it’s an ideal spot for hiking, picnicking, and immersing yourself in the natural beauty of the Blue Ridge Mountains.
Raven's Roost Overlook: Only 4 miles from Wintergreen, this romantic lookout offers breathtaking panoramic views of the mountains. Perfect for couples and nature lovers, it’s an ideal spot for photography, sunset watching, and enjoying the serene beauty of the Blue Ridge landscape.

Best time to go to Wintergreen

The best time to visit Wintergreen can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Wintergreen falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Wintergreen falls in January, 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

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
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.