- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Our top choices for Wintergreen vacation homes

1. Spacious + Serene Mtn Top Escape, 4 En Suites
Spacious + Serene Mtn Top Escape, 4 En SuitesWintergreen Resort
10.0 out of 10, Exceptional, (61 reviews)
The price is ¥15,943
¥57,593 total
includes taxes & fees
Nov 8 - Nov 9

2. 3 mins to skiing! Cozy chalet w/ king beds, fireplace, & hot tub. Dog-friendly!
3 mins to skiing! Cozy chalet w/ king beds, fireplace, & hot tub. Dog-friendly!Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
The price is ¥22,547
¥56,110 total
includes taxes & fees
Nov 8 - Nov 9

3. "Glass & Pine" Home close to Bold Rock & Vineyards
"Glass & Pine" Home close to Bold Rock & VineyardsNellysford
10.0 out of 10, Exceptional, (3 reviews)
The price is ¥29,420
¥65,767 total
includes taxes & fees
Nov 9 - Nov 10

4. The Distinguished Squirrel Chalet walking distance
The Distinguished Squirrel Chalet walking distanceTreeloft
9.2 out of 10, Wonderful, (14 reviews)
The price is ¥24,140
¥60,720 total
includes taxes & fees
Nov 10 - Nov 11

5. Blackrock Canopy
Blackrock CanopyNellysford
The price is ¥47,386
¥119,956 total
includes taxes & fees
Nov 16 - Nov 17

6. 4 BR cabin mins to trails & breweries pets welcome
4 BR cabin mins to trails & breweries pets welcomeChestnut Springs
9.6 out of 10, Exceptional, (37 reviews)
The price is ¥29,097
¥86,781 total
includes taxes & fees
Nov 11 - Nov 12

7. Walk to SKi Slopes and Hot Tub
Walk to SKi Slopes and Hot TubTreeloft
The price is ¥35,183
¥77,832 total
includes taxes & fees
Nov 8 - Nov 9

8. Wintergreen Resort, Hot Tub, Trails, and Ski!
Wintergreen Resort, Hot Tub, Trails, and Ski!Nellysford
The price is ¥35,500
¥88,597 total
includes taxes & fees
Nov 8 - Nov 9

9. The Snow House New Hot Tub Pet Friendly Creek PacMan
The Snow House New Hot Tub Pet Friendly Creek PacManWintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
The price is ¥43,075
¥90,377 total
includes taxes & fees
Nov 17 - Nov 18

10. Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game PorchChestnut Springs
9.8 out of 10, Exceptional, (20 reviews)
The price is ¥32,604
¥76,203 total
includes taxes & fees
Nov 9 - Nov 10

11. Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!Nellysford
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥59,276
¥130,060 total
includes taxes & fees
Nov 8 - Nov 9

12. Blackrock Canopy: Walk to Ski + 2 Living Spaces
Blackrock Canopy: Walk to Ski + 2 Living SpacesWintergreen Resort
The price is ¥47,386
¥127,074 total
includes taxes & fees
Nov 16 - Nov 17

13. Fall Getaway | Sauna & Hot Tub | Sleeps 14
Fall Getaway | Sauna & Hot Tub | Sleeps 14Wintergreen Resort
9.0 out of 10, Wonderful, (2 reviews)
The price is ¥26,471
¥91,180 total
includes taxes & fees
Nov 9 - Nov 10

14. Adventure Awaits
Adventure AwaitsLaurel Ridge
9.0 out of 10, Wonderful, (10 reviews)
The price is ¥41,205
¥90,732 total
includes taxes & fees
Nov 22 - Nov 23

15. Mountain Mindset
Mountain MindsetLaurel Ridge
The price is ¥47,897
¥89,161 total
includes taxes & fees
Nov 9 - Nov 10

16. Wintergreen cabin, 5 min to ski, hot tub, sauna
Wintergreen cabin, 5 min to ski, hot tub, saunaChestnut Springs
10.0 out of 10, Exceptional, (16 reviews)
The price is ¥38,255
¥76,200 total
includes taxes & fees
Nov 9 - Nov 10

17. Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort
Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen ResortRoseland
10.0 out of 10, Exceptional, (42 reviews)
The price is ¥51,506
¥132,115 total
includes taxes & fees
Nov 9 - Nov 10

18. Mountain Views in Wintergreen
Mountain Views in WintergreenLaurel Ridge
10.0 out of 10, Exceptional, (21 reviews)
The price is ¥86,174
¥162,091 total
includes taxes & fees
Nov 24 - Nov 25

19. Privacy and Views in Wintergreen
Privacy and Views in WintergreenWintergreen Resort
9.0 out of 10, Wonderful, (2 reviews)

20. Family-Friendly Meets Luxury
Family-Friendly Meets LuxuryPedlars Edge
9.4 out of 10, Exceptional, (12 reviews)
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.
Learn more about Wintergreen
Nestled in the Blue Ridge Mountains, this four-season resort offers skiing in winter and championship golf courses in summer. Hike to stunning Crabtree Falls nearby or explore the scenic Blue Ridge Parkway with its overlooks and picnic spots.



















































































