Wintergreen Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Rebecca Brent

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Wintergreen Vacation Packages

Wintergreen Hotel Deals

Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is ₩128,401 per night from Aug 3 to Aug 4
₩128,401
₩142,910 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,220 reviews)
"Staff made sure we had connected rooms that were clean."

Reviewed on Jul 23, 2025

Sleep Inn Staunton
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street, Staunton, VA
The price is ₩150,419 per night from Aug 11 to Aug 12
₩150,419
₩168,469 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
"Great location"

Reviewed on Jul 21, 2025

Hotel 24 South
Howard Johnson by Wyndham Staunton

Howard Johnson by Wyndham Staunton

2 out of 5
268 N Central Ave, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is ₩96,452 per night from Jul 29 to Jul 30
₩96,452
₩108,027 total
Jul 29 - Jul 30
includes taxes & fees
7.4/10 Good! (1,005 reviews)
"A great area to look around."

Reviewed on Jul 19, 2025

Howard Johnson by Wyndham Staunton
See all 1,200 properties in Wintergreen
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.

Discover the most popular places to visit in Wintergreen

Day off 🍺

Bold Rock Hard Cider Nellysford Cidery

You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Nellysford. Discover the mountain views in this family-friendly area.

Bold Rock Hard Cider Nellysford Cidery

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.