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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
11 Nov - 12 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, (38 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is AED 556
AED 1,346 total
includes taxes & fees
29 Nov - 30 Nov
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 682
AED 1,524 total
includes taxes & fees
16 Nov - 17 Nov
"Glass & Pine" Home close to Bold Rock & Vineyards

4. Wintergreen Ski-In/Out: Hot Tub, Sauna, Game Room

Wintergreen Ski-In/Out: Hot Tub, Sauna, Game Room
Wintergreen Resort
The price is AED 1,201
AED 2,079 total
includes taxes & fees
11 Nov - 12 Nov
Wintergreen Ski-In/Out: Hot Tub, Sauna, Game Room

5. 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 542
AED 1,381 total
includes taxes & fees
11 Nov - 12 Nov
The Distinguished Squirrel Chalet walking distance

6. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is AED 1,098
AED 2,780 total
includes taxes & fees
11 Nov - 12 Nov
Blackrock Canopy

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

Fall Getaway | Sauna & Hot Tub | Sleeps 14
Wintergreen Resort
9.0 out of 10, Wonderful, (2 reviews)
"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.
The price is AED 955
AED 2,550 total
includes taxes & fees
11 Nov - 12 Nov
Fall Getaway | Sauna & Hot Tub | Sleeps 14

8. 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 2,011 total
includes taxes & fees
11 Nov - 12 Nov
4 BR cabin mins to trails & breweries pets welcome

9. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
The price is AED 1,851
AED 3,025 total
includes taxes & fees
28 Nov - 29 Nov
Walk to SKi Slopes and Hot Tub

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

Wintergreen Resort, Hot Tub, Trails, and Ski!
Nellysford
The price is AED 1,256
AED 2,589 total
includes taxes & fees
20 Nov - 21 Nov
Wintergreen Resort, Hot Tub, Trails, and Ski!

11. 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 992
AED 2,087 total
includes taxes & fees
18 Nov - 19 Nov
The Snow House New Hot Tub Pet Friendly Creek PacMan

12. 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.
The price is AED 756
AED 1,766 total
includes taxes & fees
11 Nov - 12 Nov
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

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

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
The price is AED 1,098
AED 2,941 total
includes taxes & fees
11 Nov - 12 Nov
Blackrock Canopy: Walk to Ski + 2 Living Spaces

14. 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
11 Nov - 12 Nov
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

15. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.0 out of 10, Wonderful, (10 reviews)
"our stay was so fun! "
United States
Kaden C.
The price is AED 896
AED 2,029 total
includes taxes & fees
22 Nov - 23 Nov
Adventure Awaits

16. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AED 1,187
AED 2,158 total
includes taxes & fees
30 Nov - 1 Dec
Mountain Mindset

17. The Black Walnut - Your Own Private Resort

The Black Walnut - Your Own Private Resort
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"Great time on the property. Lots to do and eat nearby. The house has plenty of space ands lots of entertainment. Well stocked with the basics and simple check-in and checkout."
United States
Chris S.
The price is AED 2,157
AED 5,091 total
includes taxes & fees
22 Nov - 23 Nov
The Black Walnut - Your Own Private Resort

18. 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.
The price is AED 887
AED 1,758 total
includes taxes & fees
11 Nov - 12 Nov
Wintergreen cabin, 5 min to ski, hot tub, sauna

19. 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
15 Nov - 16 Nov
Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort
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