Wintergreen Holidays

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 Rp173.195 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

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 Rp1.854.292 per night from 24 Aug to 25 Aug
Rp1.854.292
Rp2.076.808 total
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Beautiful hotel"

Reviewed on 10 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 Rp2.072.444 per night from 24 Aug to 25 Aug
Rp2.072.444
Rp2.306.550 total
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (808 reviews)
"Great for a 1 night stop. Breakfast was wonderful. Very clean, would stay again!!"

Reviewed on 10 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 Rp1.840.770 per night from 21 Aug to 22 Aug
Rp1.840.770
Rp2.048.793 total
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (396 reviews)
"Wonderful single night stay at this hotel, I was uncertain where to book when there is so much choice but would 100% stay here again. We had such a warm welcome from Zoe on reception who was helpful and patient with our questions. The room was perfect for us and our three children with plenty of ..."

Reviewed on 11 Aug 2025

Holiday Inn Express And Suites Waynesboro East by IHG
See all 1,203 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.

What to do in Wintergreen

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

Rp280.556
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

Rp396.147
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

Rp214.504
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Wintergreen

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.