Wintergreen, VA
Travel Guide
Visit Wintergreen
Where to stay in Wintergreen
Chestnut Springs
Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook.
Pedlars Edge
If you're looking for some top things to see and do in Pedlars Edge and surrounding area, you can visit Wintergreen Resort and Raven's Roost Overlook.
Treeloft
When in Treeloft, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.
Laurel Ridge
When in Laurel Ridge, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.
Deer Springs
5/5(3 area reviews)
If you're looking for some top things to see and do in Deer Springs and surrounding area, you can visit Raven's Roost Overlook and Wintergreen Resort.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland VA
The price is $241 total per night from May 20 to May 21
$241 total
per night
May 20 - May 21
Stay at this condo in Wintergreen. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Raven's Roost Overlook and Wintergreen Resort are ...
9/10 Wonderful! (320 reviews)
Very clean, incredible view, jacuzzi tub is absolutely awesome. Remember to bring your own shampoo. Lots of hiking trails of varying difficulty close by. I hope to stay there again
Reviewed on Apr 23, 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
The price is $1,084 total per night from Jun 9 to Jun 10
$1,084 total
per night
Jun 9 - Jun 10
Stay at this cabin in Wintergreen. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located ...
10/10 Exceptional! (11 reviews)
Beautiful house! Gorgeous location. Easy access to hiking trails. The host is super helpful and responsive. Highly recommend!!
Reviewed on Apr 9, 2026
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! (41 reviews)
We loved being able to bring our dog with us on our long weekend mountain trip. This is an older, but cozy, comfortable and unique cabin high up on a Wintergreen mountaintop, with great views of the sunset from the big bay window and especially from the wonderful hot tub. We also enjoyed making fires ...
Reviewed on Apr 6, 2026
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.
Roseland VA
Stay at this condo in Wintergreen. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Raven's Roost Overlook and Wintergreen Resort are ...
9/10 Wonderful! (320 reviews)
Very clean, incredible view, jacuzzi tub is absolutely awesome. Remember to bring your own shampoo. Lots of hiking trails of varying difficulty close by. I hope to stay there again
Reviewed on Apr 23, 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
Stay at this cabin in Wintergreen. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located ...
10/10 Exceptional! (11 reviews)
Beautiful house! Gorgeous location. Easy access to hiking trails. The host is super helpful and responsive. Highly recommend!!
Reviewed on Apr 9, 2026
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! (41 reviews)
We loved being able to bring our dog with us on our long weekend mountain trip. This is an older, but cozy, comfortable and unique cabin high up on a Wintergreen mountaintop, with great views of the sunset from the big bay window and especially from the wonderful hot tub. We also enjoyed making fires ...
Reviewed on Apr 6, 2026
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.
Popular places to visit
Wintergreen Resort
Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.
Bold Rock Hard Cider Nellysford Cidery
You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Wintergreen. Discover the mountain views in this family-friendly area, or seek out the ski slopes.
Stoney Creek Golf Course
Enjoy a round of golf in Wintergreen at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.
Things to do
Shenandoah National Park Self-Guided Driving Audio Tour
$17
per traveler
100% of travellers recommend
Blue Ridge Parkway Virginia Self-Guided Audio Tour
$13
per traveler
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- Bold Rock Hard Cider Nellysford Cidery
- Visit Nellysford
- Stoney Creek Golf Course
- Hill Top Berry Farm & Winery
- Wintergreen Resort
- Raven's Roost Overlook
- Reids Gap Trailhead
- Flying Fox Vineyard
- Fortune's Cove Preserve
- Silverback Distillery
- Visit Tyro
- Tyro Vacations
- Delfosse Vineyards and Winery
- Mountain Cove Vineyards
- Visit Lovingston
- Cardinal Point Vineyard and Winery
- Lovingston Vacations
- Visit Massies Mill
- Afton Mountain Vineyards
- Visit Faber
- Massies Mill Vacations
- Veritas Vineyard and Winery
- Faber Vacations
- Wintergreen Resort
- Bold Rock Hard Cider Nellysford Cidery
- Stoney Creek Golf Course
- Raven's Roost Overlook
- Shenandoah National Park
- James River
- Walton's Mountain Museum
- George Washington National Forest
- Blue Ridge Parkway North Entrance
- Rockfish Gap Entrance Shenandoah
- Mary Baldwin College
- Crabtree Falls
- American Shakespeare Center
- Veritas Vineyard and Winery
- Sherando Lake Recreation Area
- Factory Antique Mall
- Frontier Culture Museum
- Pippin Hill Farm & Vineyards
- Oak Ridge Estate
- Lovingston Winery
- King Family Vineyards
- The Woodrow Wilson Presidential Library
- Afton Mountain Vineyards
- Gypsy Hill Park
- Basic City Beer Co.
- Hill Top Berry Farm & Winery
- Virginia Blue Ridge Railway Trail
- Silverback Distillery