Wintergreen Vacations from $765

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Your Wintergreen Vacation

When a break in the city is calling, answer it with a Wintergreen vacation package. The neighborhood of Laurel Ridge, which is good for skiing, adventure sports and mountain biking, makes a fantastic base for your adventures. Fill your days with visits to Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course and Hill Top Berry Farm & Winery, some of the things you simply have to see during a trip to Wintergreen. Don't delay exploring this city any longer. Your dream Wintergreen vacation is only a few clicks away with Expedia.

The Latest Wintergreen vacation packages

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $970, price is now $765 per person
$765
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
8.6/10 Excellent! (907 reviews)
The hotel itself was lovely. The rooftop dining/bar was wonderful! Conveniently located. I didn’t like that the parking was in this random lot across the train tracks. Also check in was with a QR code and I had to download my license and take a selfie which I found annoying since there was a human being right there to check me in. Why the lack of human contact. Other than that the hotel was lovely.

Reviewed on Oct 7, 2025

Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
Price was $1,155, price is now $929 per person
$929
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.6/10 Exceptional! (375 reviews)
Wonderful hotel and restaurants for a football weekend!

Reviewed on Sep 28, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,018, price is now $819 per person
$819
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (485 reviews)
Staff was so kind and the property was gorgeous. I travel for work and this was one of my favorite places I have stayed.

Reviewed on Sep 30, 2025

Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
Price was $1,097, price is now $909 per person
$909
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (1,007 reviews)
Great location and beautiful room!

Reviewed on Oct 10, 2025

Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Venable
Price was $1,031, price is now $869 per person
$869
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
8.2/10 Very Good! (1,002 reviews)
Front desk staff want very welcoming. Parking is limited. The hotel seems dark and dated and definitely needs some renovation. They are in the process of doing that now so some noise related to that….I might stay there again but not until the renovations are done. In the meantime, I’d stay elsewhere.

Reviewed on Oct 5, 2025

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

Wintergreen Resort
Day off 🍺

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 Nellysford. Discover the mountain views in this family-friendly area.

Bold Rock Hard Cider Nellysford Cidery

Stoney Creek Golf Course

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

Stoney Creek Golf Course

What to do in Wintergreen

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

$24
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$16
per traveler
Shenandoah National Park Self-Guided Audio Tour
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
See all activities in Wintergreen

Wintergreen Hotel Deals

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland
10/10 Exceptional! (326 reviews)
"Comfortable clean and quiet place to stay during the beginning of October."

Reviewed on Oct 9, 2025

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Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Wintergreen Resort
$635 nightly
The price is $713 total per night from Oct 14 to Oct 15
$713 total
Oct 14 - Oct 15
Total with taxes and fees
10/10 Exceptional! (62 reviews)
"Beautiful rental “in the tree tops” with many thoughtful and modern accommodations! The host takes extra efforts to provide a detailed list online of how to use the rental and what activities there are nearby. We absolutely loved our stay here."

Reviewed on Sep 26, 2025

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
The Modern Mountain Condo

The Modern Mountain Condo

Wintergreen Resort
$224 nightly
The price is $251 total per night from Oct 15 to Oct 16
$251 total
Oct 15 - Oct 16
Total with taxes and fees
9.8/10 Exceptional! (28 reviews)
"Great little condo for a quick getaway for a wedding. Spent very little time in the unit, but convenient, affordable and very clean!"

Reviewed on Oct 1, 2025

The Modern Mountain Condo
See all 1,233 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.

Wintergreen Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)
Population
170
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course

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Frequently asked questions

How much does a Wintergreen vacation package cost?
You'll find cheap prices from $765 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?
July, November and December are great times to look for cheap Wintergreen vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on hotels and flights.
How many days is enough for Wintergreen?
With a well-planned itinerary, you can easily tick off the main Wintergreen attractions in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Wintergreen vacation for longer.
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 when to go: Check your diary and get your bags packed. Your favorite season and the activities available will also help you decide when to escape to Wintergreen.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Wintergreen.
  3. Use our trip planning tool to discover Wintergreen: Research every part of your trip to Wintergreen with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go away for: Now that you know more about Wintergreen, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Wintergreen vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Wintergreen's best offerings. Find all the exciting things to do in Wintergreen in Wintergreen with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Wintergreen vacation packages?
Your Wintergreen getaway should be an escape from your daily routine, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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