Wintergreen, VA

Travel Guide

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.
A mountainous landscape with lush green hills and a clear blue sky with contrails.
A snow-covered mountain landscape with a ski resort and a clear blue sky.
A mountainous landscape with dense forests and a valley.
A stone tunnel with moss-covered walls and a rocky hillside.
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 9 to Nov 10
$237 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this condo in Wintergreen. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are ...
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
Stay at this cabin in Wintergreen. Enjoy private hot tubs, laundry facilities, and tennis courts. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
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
Stay at this vacation home in Wintergreen. Enjoy free WiFi, 2 outdoor pickleball courts, and a fitness center. Popular attractions Wintergreen Resort and Raven's ...
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.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

Roseland VA
Stay at this condo in Wintergreen. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are ...
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
Stay at this cabin in Wintergreen. Enjoy private hot tubs, laundry facilities, and tennis courts. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
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

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
Stay at this vacation home in Wintergreen. Enjoy free WiFi, 2 outdoor pickleball courts, and a fitness center. Popular attractions Wintergreen Resort and Raven's ...
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

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

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.
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Things to do

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

Frequently asked questions

Is Wintergreen worth visiting?
Wintergreen is worth visiting for its distinct areas to explore, such as Chestnut Springs. Travelers can also enjoy standout attractions like the Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery, offering unique experiences in the region.
When is the best time to visit Wintergreen?
The best time to visit Wintergreen is from December through February, when the destination is most popular. For fewer crowds and better value, the quieter months of April through June are a good option, offering a different experience with milder weather.
Where are the best neighborhoods to explore in Wintergreen?
The best neighborhoods to explore in Wintergreen depend on what you want to see:

  • Chestnut Springs offers travelers attractions like High Ridge, Timbers, and Highridge Court.

What is Wintergreen known for?
Wintergreen is known for its prominent Wintergreen Resort, offering travelers a place to stay and enjoy the area. Travelers can also visit the Bold Rock Hard Cider Nellysford Cidery and play a round at Stoney Creek Golf Course. The city features neighborhoods like Chestnut Springs.
What is a good itinerary length for Wintergreen?
A good itinerary length for Wintergreen is two to three days to enjoy Wintergreen Resort, visit Bold Rock Hard Cider Nellysford Cidery, and play at Stoney Creek Golf Course. For an extended stay of four to five days, travelers can explore the Chestnut Springs area more deeply and enjoy a more relaxed pace.
What are the top things to do in and around Wintergreen?
Wintergreen offers outdoor activities, scenic views, and local flavors for travelers to enjoy:


How do I plan a trip to Wintergreen?
To plan your trip to Wintergreen, book flights, hotels, and rental cars in advance. Consider staying in Chestnut Springs to be near attractions like Wintergreen Resort, Bold Rock Hard Cider Nellysford Cidery, and Stoney Creek Golf Course. When planning activities, pair outdoor options with indoor backups for weather flexibility.
Can I book a refundable hotel in Wintergreen?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Wintergreen by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Wintergreen with Expedia?
Expedia makes it easier to plan your Wintergreen trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Wintergreen?
The best choice depends on your travel style. Hotels in Wintergreen can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Wintergreen trip on Expedia?
Once you've booked your Wintergreen trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Wintergreen trip?
Expedia offers customer support before, during, and after your Wintergreen trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Wintergreen?
If it's your first trip to Wintergreen, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Wintergreen hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Wintergreen hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Wintergreen

A lake reflecting colorful autumn trees, a clear sky, and a hilly landscape.

Lyndhurst

A stone tunnel with moss-covered walls and a rocky hillside.

Nellysford

A mountainous landscape with dense green forests and rocky outcrops.

Faber

A gravel road curving through a green field with a wooden fence on one side and mountains in the background.

Roseland

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