Wintergreen Holidays

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Our guide on where to stay in Wintergreen

Find the best Wintergreen areas and neighborhoods for the activities you enjoy most. Learn more about Wintergreen
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Chestnut Springs

While Chestnut Springs may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wintergreen Resort and Raven's Roost Overlook.

Find hotels in Chestnut Springs

Wintergreen Holiday

Our pick of the best Wintergreen Hotel Deals

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA
The price is NZ$439 per night from 20 July to 21 July
NZ$439
20 July - 21 July
includes taxes & fees
Endless Mountain Top Views from All The Way Up!
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland VA
The price is NZ$470 per night from 26 July to 27 July
NZ$470
26 July - 27 July
includes taxes & fees
9/10 Wonderful! (325 reviews)
"I didn't have a good experience here. Some things I could have dealt with, like the hot tub was unreasonably loud, and there was a Keurig but no coffee. However, I had two major issues. One is that the back wall is entirely floor to ceiling windows, but only half of the windows had functional curtains. ..."

Reviewed on 11 June 2026

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
10/10 Exceptional! (18 reviews)
"The cabin was a perfect place to stay. Clean, roomy, and had all of the amenities. Troy was an excellent host and very responsive. We would absolutely come back to stay here."

Reviewed on 9 July 2026

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New Build! Log Cabin with Hot Tub in Wintergreen
See all 669 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.

Stay near popular Wintergreen attractions

A waterfall in a forest with autumn leaves.

Wintergreen Resort

8.8/10 (140 reviews)
Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.
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What to do in Wintergreen

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

NZ$42
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

NZ$23
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.

Explore a world of travel with Expedia

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