Wintergreen Vacations from $491

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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.
Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Save 100% on your flight
Price was $737, price is now $491 per person
$491
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
8.6/10 Excellent! (59 reviews)
It was a lodge and it was picturesque on water and all around. It was pastures full of beautiful horses. The rooms were really small but they worked and the one thing that I was surprised is when I paid through Expedia I thought I was paid 100% but when I got there, they charge a $25 per day resort fee. Because they also have an RV and cabins and they have a playground basketball court things like that so I guess they charge a resort fee personally it should just be part of the rental so you’re not getting any surprise charges when you get there, otherwise it was lovely and I would actually consider going back there.

Reviewed on Oct 21, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Save 100% on your flight
Price was $1,030, price is now $713 per person
$713
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
9.2/10 Wonderful! (496 reviews)
Such a cool venue with excellent service. You can't beat the location if you are coming for anything with UVA! The staff, parking, atmosphere, pool area, live entertainment - all exceptional. I will stay again on my next visit!

Reviewed on Oct 21, 2025

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $740, price is now $518 per person
$518
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
8.2/10 Very Good! (818 reviews)
We were in 2 bedroom cabin, very clean and comfortable. Pretty property, well maintained. Only there 2 days, would love to go back.

Reviewed on Oct 12, 2025

Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Venable
Save 100% on your flight
Price was $919, price is now $646 per person
$646
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
8.2/10 Very Good! (1,002 reviews)
Close to the college. Room was barely clean.

Reviewed on Oct 20, 2025

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Save 100% on your flight
Price was $849, price is now $597 per person
$597
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
8.6/10 Excellent! (926 reviews)
The property was a very cute boutique style hotel. Loved the lobby and the artwork and style aesthetic. Nice rooftop fire pit setup. Beds were very comfortable. Very quiet stay.

Reviewed on Oct 17, 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 Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

$13
per traveler
Blue Ridge Parkway Virginia Self-Guided 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! (327 reviews)
Was the perfect place for us! Loved that there was a fireplace, made it super cozy!

Reviewed on Oct 15, 2025

Get rates
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

Wintergreen Resort
We had a fabulous stay at Warren’s Woods! The location of the house is perfectly situated within Wintergreen, a short walk or drive to hiking and the main resort facilities. We enjoyed the hot tub and wood burning fireplace. The kitchen was very well stocked and the layout of the house was great ...

Reviewed on Oct 12, 2025

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NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
The Modern Mountain Condo

The Modern Mountain Condo

Wintergreen Resort
$216 nightly
The price is $243 total per night from Oct 26 to Oct 27
$243 total
Oct 26 - Oct 27
Total with taxes and fees
9.8/10 Exceptional! (30 reviews)
Very nice! Great place.

Reviewed on Oct 13, 2025

The Modern Mountain Condo
See all 1,235 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.

Find the Best Wintergreen Vacation Packages

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 $491 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.