Wintergreen Vacations

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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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Treeloft

When in Treeloft, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.

Find hotels in Treeloft

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 AED 380 per night from Feb 11 to Feb 12
AED 380
AED 930 total
11 Feb - 12 Feb
includes taxes & fees
9/10 Wonderful! (298 reviews)
Excellent view. Great location

Reviewed on 21 January 2026

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Cozy Cabin with private HOT TUB!

Cozy Cabin with private HOT TUB!

Nellysford VA
10/10 Exceptional! (34 reviews)
We enjoyed our visit. Beautiful cabin, very quiet and peaceful.

Reviewed on 11 January 2026

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Cozy Cabin with private HOT TUB!
The Modern Mountain Condo

The Modern Mountain Condo

Wintergreen Resort VA
The price is AED 385 per night from Mar 5 to Mar 6
AED 385
AED 886 total
5 Mar - 6 Mar
includes taxes & fees
9.8/10 Exceptional! (41 reviews)
Excellent location, walked right over to the top of the slopes and about 30 yards from the market. Everything was clean, in good working order and perfect for our party of three

Reviewed on 24 January 2026

The Modern Mountain Condo
See all 674 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.

Discover the most popular places to visit in Wintergreen

Everything is frozen over at Wintergreen Resort.

Wintergreen Resort

4.5/5(79 reviews)

Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.

Wintergreen Resort

Bold Rock Hard Cider Nellysford Cidery

4.5/5(6 reviews)

You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Wintergreen. Discover the mountain views in this family-friendly area, or seek out the ski slopes.

Bold Rock Hard Cider Nellysford Cidery

Stoney Creek Golf Course

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

Stoney Creek Golf Course

Frequently asked questions

How do I find cheap flights to Wintergreen that have flexible change policies?
Search for your cheap fares to Wintergreen, then check the "No change fee" box underneath the "Flexible change policies" heading. It's that simple. We appreciate that plans change and flexibility is essential, so book with confidence with Expedia.
Which airlines fly to Wintergreen?
Figure out your vacation dates and then take off towards Wintergreen with one of these leading airlines:

  • American Airlines - 286 flights to or near Wintergreen each month, including 286 flights to Charlottesville-Albemarle Airport (CHO) per month.
  • United Airlines - 138 flights to or near Wintergreen each month, including 138 flights to Charlottesville-Albemarle Airport (CHO) per month.
  • Delta Air Lines - 78 flights to or near Wintergreen each month, including 78 flights to Charlottesville-Albemarle Airport (CHO) per month.

How can I find cheap tickets to Wintergreen?
One of the easiest ways to get a hold of cheap tickets to Wintergreen is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It will bring up the cheapest prices for nearby days. The best price for a flight to Wintergreen in the last seven days was . Booking ahead of time will generally help you get an even better deal.
How much is a flight to Wintergreen?
There were plenty of affordable fares up for grabs in the last seven days, with the price of a return ticket to Wintergreen ranging between and . Many lucky vacationers purchased one-way seats from () for as little as .
What are the most popular airports to fly into in Wintergreen?
Get ready to pack your suitcase and fly into Charlottesville-Albemarle Airport (CHO), Wintergreen's leading flight hub. Lock in a seat on one of the 502 flights that land at this favorite destination each month.
When is the cheapest time to fly to Wintergreen?
If you can be flexible with what date you jet off to Wintergreen, leave early on in the week. The cheapest day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the priciest day, with many vacationers opting to fly on the weekend.
How much is a plane ticket to Wintergreen?
Prices varied from to in the last seven days. When you're ready to book, we'll help you secure a fabulous deal to Wintergreen.
What months are the cheapest to book a flight to Wintergreen?
Snap up a ticket in February to unlock incredible flight deals to Wintergreen. The month of December is known as the most expensive time to purchase an airfare.
How long is a flight to Wintergreen?
Flight durations can vary for a lot of different reasons, including where you're coming from. We've put together a list of average flight times for some of the busiest domestic routes to Wintergreen:

  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Charlottesville-Albemarle Airport (CHO) - 1 hour and 22 minutes
  • New York, NY (LGA-LaGuardia) to Charlottesville-Albemarle Airport (CHO) - 1 hour and 34 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Charlottesville-Albemarle Airport (CHO) - 1 hour and 34 minutes