Wintergreen Vacations from $528

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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.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
9.2/10 Wonderful! (2,264 reviews)
It worked fine but was rough needed some TLC and clearly half ass cleaned. But it was the cheapest around that's for sure.....

Reviewed on Jul 9, 2025

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Charlottesville (CHO)
9.4/10 Exceptional! (273 reviews)
An absolutely lovely stay. A treat to stay in this historic inn. Very quiet, lovely room, great bed and a nice breakfast at the Farm Bell Kitchen. Tea and coffee always available with a nice touch to offer wine for sale as well. Easy walk to the campus and to get around the Charlottesville area. I’d definitely stay again.

Reviewed on Jul 7, 2025

Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Charlottesville (CHO)
9.6/10 Exceptional! (337 reviews)
We have stayed here before and really love the amenities the decor, the architecture and most of all the friendly staff especially Catherine, Taylor, and Cortney. The food is really delicious.

Reviewed on Jul 6, 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Charlottesville (CHO)
9.2/10 Wonderful! (224 reviews)
The place has a great location, the staff was super friendly and helpful and the room was cute . Despite two window shades ( presumably one was room darkening) the outside light made our room much less dark than we would have preferred for sleeping .

Reviewed on Jul 10, 2025

Hollymead House

Hollymead House

2 out of 5
Hollymead
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Charlottesville (CHO)
10/10 Exceptional! (6 reviews)
I enjoyed staying at Hollymead for a wedding weekend. I would definitely stay in the guest house again. The owners were very welcoming and the room was so comfortable.

Reviewed on Oct 24, 2022

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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

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
Sharp Top Mountain

Blue Ridge Parkway Virginia Self-Guided Audio Tour

$13
per traveler
Blue Ridge Parkway Virginia Self-Guided Audio Tour
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$15
per traveler
Shenandoah National Park Self-Guided Audio Tour
See all activities in Wintergreen

Wintergreen Hotel Deals

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Roseland
$342 nightly
The price is $384 total per night from Jul 14 to Jul 15
$384 total
Jul 14 - Jul 15
Total includes taxes and fees
9.6/10 Exceptional! (259 reviews)
Summer Vacation
"The house was just as described. Scott was very quick to respond and always pleasant. The hot tub was very nice and the house is set in a beautiful wooded area close to pools and a convenience store. Would definitely rent the house again."

Reviewed on Jun 29, 2025

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Wintergreen
9.8/10 Exceptional! (220 reviews)
Mother/daughter getaway
"Beautiful, clean, comfortable, spectacular views. The property was exactly as advertised and pictures were accurate. Kitchen had everything you need if you decide to cook-in. Pots and pans in great shape. This was the best of any rental that we have stayed in. It is a lovely property. Highly recommend ..."

Reviewed on May 20, 2025

Get rates
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
$414 nightly
The price is $465 total per night from Jul 13 to Jul 14
$465 total
Jul 13 - Jul 14
Total includes taxes and fees
9.8/10 Exceptional! (19 reviews)
Perfect location
"We had such a great girls weekend!! The Cottage was so cute, fun, clean and beds were super comfy. The house was in the perfect location for everything. Can’t wait to go back."

Reviewed on Mar 10, 2025

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
See all 1,193 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 $528 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.