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Our top choices for Wintergreen vacation homes

1. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (61 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
The price is AED 370
AED 1,335 total
includes taxes & fees
8 Nov - 9 Nov
Spacious + Serene Mtn Top Escape, 4 En Suites

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, (37 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
3 mins to skiing! Cozy chalet w/ king beds, fireplace, & hot tub. Dog-friendly!

3. "Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Great house and location near lots of activities. The home was very clean and the kitchen was well stocked. Very nice to sit and relax on the deck. The host was quick to respond to any questions and communication was great. Definitely recommend if you are looking to stay somewhere along 151 or near Wintergreen."
United States
Dean G.
The price is AED 955
AED 1,823 total
includes taxes & fees
18 Nov - 19 Nov
"Glass & Pine" Home close to Bold Rock & Vineyards

4. The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.2 out of 10, Wonderful, (14 reviews)
"Great location and the slopes are easily accessible!"
United States
Mark H.
The price is AED 598
AED 1,460 total
includes taxes & fees
18 Nov - 19 Nov
The Distinguished Squirrel Chalet walking distance

5. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is AED 1,146
AED 2,834 total
includes taxes & fees
18 Nov - 19 Nov
Blackrock Canopy

6. 4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (37 reviews)
"it is really excellent."
United States
RK D.
The price is AED 674
AED 1,933 total
includes taxes & fees
18 Nov - 19 Nov
4 BR cabin mins to trails & breweries pets welcome

7. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
The price is AED 981
AED 1,998 total
includes taxes & fees
18 Nov - 19 Nov
Walk to SKi Slopes and Hot Tub

8. Wintergreen Resort, Hot Tub, Trails, and Ski!

Wintergreen Resort, Hot Tub, Trails, and Ski!
Nellysford
The price is AED 823
AED 2,066 total
includes taxes & fees
8 Nov - 9 Nov
Wintergreen Resort, Hot Tub, Trails, and Ski!

9. The Snow House New Hot Tub Pet Friendly Creek PacMan

The Snow House New Hot Tub Pet Friendly Creek PacMan
Wintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
"Great time, great location and very smooth process. Looking forward to planning another stay next ski season. "
United States
Justin L.
The price is AED 1,021
AED 2,042 total
includes taxes & fees
18 Nov - 19 Nov
The Snow House New Hot Tub Pet Friendly Creek PacMan

10. Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
9.8 out of 10, Exceptional, (20 reviews)
"Great stay!"
United States
Cheryl P.
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

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)
"We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!"
United States
Rachel F.
The price is AED 1,382
AED 3,120 total
includes taxes & fees
8 Nov - 9 Nov
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

12. Blackrock Canopy: Walk to Ski + 2 Living Spaces

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
The price is AED 1,146
AED 2,986 total
includes taxes & fees
18 Nov - 19 Nov
Blackrock Canopy: Walk to Ski + 2 Living Spaces

13. Fall Getaway | Sauna & Hot Tub | Sleeps 14

Fall Getaway | Sauna & Hot Tub | Sleeps 14
Wintergreen Resort
8.0 out of 10, Very good, (1 review)
"We enjoyed our stay at the 7th hole chalet and would return. The house is spacious and was clean and included everything we needed. It did seem to have a lot of extra, unnecessary furniture in some of the rooms and pictures weren't exactly like listing. The landscaping was overgrown and messy out front. There are lots of controls for the heating and air throughout the house, but they are very hard to use and no instructions posted. The hot tub was nice and enjoyed by our crew, but the cover lift...
United States
Paula L.
Fall Getaway | Sauna & Hot Tub | Sleeps 14

14. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.0 out of 10, Wonderful, (10 reviews)
"our stay was so fun! "
United States
Kaden C.
Adventure Awaits

15. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AED 1,087
AED 2,045 total
includes taxes & fees
9 Nov - 10 Nov
Mountain Mindset

16. Wintergreen cabin, 5 min to ski, hot tub, sauna

Wintergreen cabin, 5 min to ski, hot tub, sauna
Chestnut Springs
10.0 out of 10, Exceptional, (16 reviews)
"Family friendly in every way possible! My friends and I had the best experience with the nearby hikes, overlooks, and overall destination of the home! Awesome place to stay!"
United States
mikenzi b.
Wintergreen cabin, 5 min to ski, hot tub, sauna

17. Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort

Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (42 reviews)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
The price is AED 1,194
AED 3,062 total
includes taxes & fees
9 Nov - 10 Nov
Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort

18. Mountain Views in Wintergreen

Mountain Views in Wintergreen
Laurel Ridge
10.0 out of 10, Exceptional, (21 reviews)
"Thank you for a nice stay. "
United States
Peter D.
Mountain Views in Wintergreen

19. Privacy and Views in Wintergreen

Privacy and Views in Wintergreen
Wintergreen Resort
9.0 out of 10, Wonderful, (2 reviews)
"This place is beautiful and family friendly! The host was great. If we had a concern, the host responded immediately and resolved. "
United States
Anna C.
Privacy and Views in Wintergreen

20. Family-Friendly Meets Luxury

Family-Friendly Meets Luxury
Pedlars Edge
9.4 out of 10, Exceptional, (12 reviews)
"Perfect for a family gathering with kids! Awesome amenities."
United States
James B.
Family-Friendly Meets Luxury
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.

A mountainous landscape with lush green hills and a clear blue sky with contrails.

Top reviews in Wintergreen