Wintergreen Vacations from $599

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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 $684, price is now $599 per person
$599
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
8.2/10 Very Good! (1,008 reviews)
The Doyle property is amazing and the rooftop is spectacular. Bartenders are attentive and amusing! Highly recommend the Doyle. Short walk to downtown mall. Hours of fun

Reviewed on Nov 9, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $765, price is now $658 per person
$658
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
9.2/10 Wonderful! (630 reviews)
Wonderful! The room, staff, location, cleanliness…. All wonderful! I’ll definitely come back!

Reviewed on Nov 8, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Price was $769, price is now $663 per person
$663
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
9.8/10 Exceptional! (153 reviews)

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $912, price is now $807 per person
$807
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
9.6/10 Exceptional! (446 reviews)
We spent three days in Charlottesville and stayed at the Dinsmore. The location was excellent, with free public bus service to downtown and the mall within steps of the Inn. Our room was very large, immaculate and well appointed. We were greeted by the manager who made it clear he was available if there was anything we needed (we need a wine opener). Parking was free and immediately adjacent to the Inn. Breakfast was amazing. We couldn't have asked for a better place to stay.

Reviewed on Nov 5, 2026

Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
Price was $777, price is now $690 per person
$690
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
9.6/10 Exceptional! (1,146 reviews)

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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
A person taking a photo of a mountainous landscape with a wooden fence in the foreground.

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

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

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

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland VA
$211 nightly
The price is $237 total per night from Nov 10 to Nov 11
$237 total
Nov 10 - Nov 11
Total with taxes and fees
9/10 Wonderful! (339 reviews)
"My wife Teresa and I have been renting this condo for 12 yrs in a row. For the money, its the best rental in Wintergreen! Already booked and paid for for next year's visit. Accessibility is another plus with this condo that no one ever mentions. we are both 60 yrs old so this is important and if ..."

Reviewed on Oct 24, 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! (53 reviews)
"Better than I expected. Clean very streamlined check-in/out process. Only negative comment is the app is cumbersome to modify and was not able to cancel my last day stay."

Reviewed on Oct 24, 2026

Get rates
Cozy Cabin with private HOT TUB!
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Wintergreen Resort VA
9.8/10 Exceptional! (9 reviews)
"We had a lovely experience staying at this property. We stayed two nights with our 3 kids (ages 5, 7, 9) and we all thoroughly enjoyed the hot tub, Pac Mac console and enjoyed making a fire and roasting s'mores. The house was very clean, beds were comfortable and communication was prompt. We did ..."

Reviewed on Oct 20, 2026

Get rates
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
See all 652 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

Things to do near Wintergreen

Wintergreen offers an exciting blend of outdoor adventures and sports, making it a perfect vacation spot. Visitors can enjoy skiing on the ski fields, take scenic chairlift rides, or engage in mountain biking. For family-friendly fun, mini golf and disc golf are available. Don't forget to make activity reservations at the resort to fully experience all that Wintergreen has to offer.

Shopping

In Wintergreen, you can shop at local boutiques and gift shops for unique souvenirs. If you're up for a drive, Windmill Square is 13 miles away, offering a variety of shops. Staunton Mall and Orchard Hill Square Shopping Center, both 19 miles away, provide a wider selection for your shopping needs.

Recreation

At Stoney Creek Golf Course, enjoy a round of golf surrounded by scenic landscapes and outdoor vibes, located 1 mile from Wintergreen. For relaxation, head to Sherando Lake Recreation Area, 7 miles away, where you can unwind amidst nature's tranquility. Experience culture and entertainment at Wayne Theatre, 13 miles from Wintergreen.

Adventure

At Wintergreen Resort, enjoy skiing on pristine slopes with breathtaking views, just 3 miles from Wintergreen. For hiking enthusiasts, the Reids Gap Trailhead offers scenic trails and outdoor adventure, located 5 miles away. Don't miss a visit to Caromont Farm, 15 miles away, for a unique farm experience.

Nightlife

Wintergreen offers a cozy nightlife with venues like The Edge Restaurant & Lounge, perfect for a relaxed dinner and drinks. For live music and entertainment, check out the nearby Wintergreen Resort. Enjoy the stunning mountain views while sipping cocktails and socializing with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Wintergreen

Wintergreen, Virginia, is an ideal destination for ski enthusiasts and adventure seekers. Explore a variety of attractions, including ski resorts, museums, and historic houses that offer a blend of culture and outdoor experiences. Whether you’re hitting the slopes or delving into local history, Wintergreen provides plenty of activities for every traveler. Don't miss out on the unique wintergreen attractions that enhance your visit to this charming area.

  • Wintergreen Resort: Experience the thrill of skiing at Wintergreen Resort, a premier destination just 3 miles away. With its stunning slopes and outdoor adventure vibes, this resort promises fun for all skill levels, making it perfect for families and thrill-seekers alike.
  • Blue Ridge Parkway North Entrance: Located 10 miles away, this visitor center welcomes you with outdoor adventure and family-friendly activities. Enjoy breathtaking views and learn about the natural beauty of the Blue Ridge Mountains while soaking up the area's rich history.
  • Raven's Roost Overlook: A scenic lookout just 4 miles from Wintergreen, Raven's Roost Overlook offers romantic vistas and adventure vibes. It's an ideal spot for couples to share a moment while taking in the stunning panoramic views of the surrounding landscape.

Best time to go to Wintergreen

The best time to visit Wintergreen is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.4°F (0.8°C)Light RainMostly SunnyModerately HighSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyModerately HighSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageAverage
April54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
May64.0°F (17.8°C)Light RainMostly SunnyModerately LowSlightly High
June72.1°F (22.3°C)Light RainMostly SunnyModerately LowAverage
July76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
August74.3°F (23.5°C)Light RainMostly SunnyModerately LowAverage
September68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageSlightly High
November44.8°F (7.1°C)Light RainMostly SunnyAverageSlightly High
December38.5°F (3.6°C)Light RainMostly SunnyModerately HighSlightly Low

Tips to save on your trip to Wintergreen

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Wintergreen.
  • Consider traveling to Wintergreen during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What's included in a Wintergreen vacation package?
A Wintergreen vacation package lets you combine round-trip flights, hotel stays, and rental cars for a convenient trip. For this outdoor destination known for skiing, most hotels offer ski-in/ski-out access, making it easy to hit the slopes. A small share of hotels provide airport shuttle service to and from airports like Richmond International Airport (RIC), and around 1 in 3 hotels include free breakfast to start your day.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Wintergreen vacation package?
When you bundle, you can save up to 30%*. To save money on a Wintergreen package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Wintergreen?
Wintergreen is an outdoor and nature destination, offering a range of activities centered around its scenic mountain setting. A Wintergreen vacation can include:

Browse and book things to do in Wintergreen on Expedia.
Do you need to rent a car in Wintergreen, or is public transport enough?
Wintergreen is an outdoor and nature destination located outside a city, primarily known for skiing, making a rental car highly recommended for exploring the area. While your Wintergreen vacation package with flights will get you to the region, attractions like Wintergreen Resort, Shenandoah National Park, and Smith Mountain Lake are spread out. Having a car provides the flexibility to visit various trailheads, vineyards, and scenic overlooks at your own pace.

Many resorts in areas like Pedlars Edge and Treeloft offer on-site dining and activities, so a car might not be essential for daily needs within the resort itself. However, for day trips to places like Afton Mountain Vineyards or Sherando Lake Recreation Area, a car is the most practical option. The nearest major airports include Richmond International Airport (RIC) and Roanoke Regional Airport (ROA).
Can I change or cancel my Wintergreen vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Wintergreen vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Wintergreen vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Wintergreen vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Wintergreen?
To find last-minute vacation packages to Wintergreen, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Wintergreen vacation packages?
Free cancellation on a Wintergreen vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Wintergreen vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Wintergreen getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Wintergreen vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.