Wintergreen Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rebecca Brent

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to Rp173.195 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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 Rp1.777.317 per night from 13 Jul to 14 Jul
Rp1.777.317
Rp1.990.596 total
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Beautiful property with the pools,ocean, restaurant facility, small store, beautiful grounds, friendly staff"

Reviewed on 24 Jun 2025

Hotel 24 South
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 Rp1.517.162 per night from 6 Jul to 7 Jul
Rp1.517.162
Rp1.688.602 total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,181 reviews)
"Felt comfortable"

Reviewed on 25 Jun 2025

Sleep Inn Staunton
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 Rp1.799.199 per night from 30 Jun to 1 Jul
Rp1.799.199
Rp2.002.509 total
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (356 reviews)
"Breakfast options could have been better. Include better quality fruits and variety."

Reviewed on 24 Jun 2025

Holiday Inn Express And Suites Waynesboro East by IHG
See all 1,198 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.

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.

What to do in Wintergreen

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

Rp276.342
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

Rp406.462
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

Rp211.282
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Wintergreen
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.