Wintergreen Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rebecca Brent

Top hotels in Wintergreen

Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is 2.992.381 ₫ per night from 1 Sept to 2 Sept
2.992.381 ₫
3.351.467 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Everything perfect."

Reviewed on 13 Aug 2025

Hotel 24 South
Holiday Inn Express And Suites Staunton by IHG

Holiday Inn Express And Suites Staunton by IHG

2.5 out of 5
47 Rolling Thunder Lane, Staunton, VA
Fully refundable
The price is 2.970.276 ₫ per night from 31 Aug to 1 Sept
2.970.276 ₫
3.305.795 ₫ total
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (809 reviews)
"Very nice and new with courteous and friendly staff"

Reviewed on 15 Aug 2025

Holiday Inn Express And Suites Staunton by IHG
Holiday Inn Express And Suites Waynesboro East by IHG

Holiday Inn Express And Suites Waynesboro East by IHG

2.5 out of 5
108 Chicurel Lane, Waynesboro, VA
Fully refundable
The price is 2.968.736 ₫ per night from 21 Aug to 22 Aug
2.968.736 ₫
3.304.229 ₫ total
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (400 reviews)
recommended
"Easy, clean and comfortable. Good breakfast a bonus."

Reviewed on 14 Aug 2025

Holiday Inn Express And Suites Waynesboro East by IHG
See all 1,191 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.

Popular places to visit

Bold Rock Hard Cider Nellysford Cidery

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

Stoney Creek Golf Course

Enjoy a round of golf in Nellysford at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.

Stoney Creek Golf Course

Hill Top Berry Farm & Winery

You can enjoy a tasting or tour at Hill Top Berry Farm & Winery during your travels to Nellysford. Discover the mountain views and top-notch restaurants in this vibrant area.

Hill Top Berry Farm & Winery

Frequently asked questions

How much does a Wintergreen holiday 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 holiday to Wintergreen costs.
What are the cheapest months to go to Wintergreen?
If you'd like to score a cheap Wintergreen holiday package, consider travelling in March, April and August. You'll generally find better rates on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Wintergreen?
The ideal duration of your Wintergreen holiday 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 holiday as a package?
You can enjoy significant savings on your next Wintergreen break by booking a customised holiday 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 holiday 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 holiday. 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 holiday package that brings all your bookings together.