Wintergreen Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Where to stay in Wintergreen

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

Chestnut Springs

Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook.

Find hotels in Chestnut Springs

Find the Best Wintergreen Vacation Packages

Wintergreen Hotel Deals

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 ￥17,134 per night from Jul 13 to Jul 14
￥17,134
￥41,708 total
Jul 13 - Jul 14
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 Jun 11, 2026

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA
The price is ￥15,211 per night from Jul 7 to Jul 8
￥15,211
￥42,266 total
Jul 7 - Jul 8
includes taxes & fees
10/10 Exceptional! (109 reviews)
"We absolutely loved the location of this property. The views are stunning and unobstructed from the balcony. We enjoyed the fireplace and the view from inside the main living area as well. We booked this location as a halfway point to Maggie Valley and my husband (and our kids too) agree that this ..."

Reviewed on Jun 16, 2026

Endless Mountain Top Views from All The Way Up!
Cozy Cabin with private HOT TUB!

Cozy Cabin with private HOT TUB!

Nellysford VA
10/10 Exceptional! (45 reviews)
"The Hut tub was the best! Everything was working properly. The hot tub was clean and so convenient right out on the deck. The front porch was out favorite. The rockers out there were nice. It would be nice if there were comfortable chairs on the back patio to be able to sit and visit and hang out. ..."

Reviewed on Jun 11, 2026

Get rates
Cozy Cabin with private HOT TUB!
See all 664 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.
See properties

What to do in Wintergreen

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

￥3,837
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

￥2,718
per traveler
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

￥2,078
per traveler
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Wintergreen

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.

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.