A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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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
3 Nov - 4 Nov
Spacious + Serene Mtn Top Escape, 4 En Suites

2. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! 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.
The price is AED 572
AED 1,307 total
includes taxes & fees
18 Nov - 19 Nov
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! 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 876
AED 1,786 total
includes taxes & fees
3 Dec - 4 Dec
"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 608
AED 1,473 total
includes taxes & fees
9 Nov - 10 Nov
The Distinguished Squirrel Chalet walking distance

5. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is AED 1,098
AED 2,780 total
includes taxes & fees
3 Nov - 4 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 2,024 total
includes taxes & fees
3 Nov - 4 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 823
AED 1,874 total
includes taxes & fees
3 Nov - 4 Nov
Walk to SKi Slopes and Hot Tub

8. 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 2,100 total
includes taxes & fees
3 Nov - 4 Nov
The Snow House New Hot Tub Pet Friendly Creek PacMan

9. 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.
The price is AED 1,104
AED 2,808 total
includes taxes & fees
3 Nov - 4 Nov
Fall Getaway | Sauna & Hot Tub | Sleeps 14

10. 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 2,933 total
includes taxes & fees
3 Nov - 4 Nov
Blackrock Canopy: Walk to Ski + 2 Living Spaces

11. 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 777
AED 1,844 total
includes taxes & fees
4 Nov - 5 Nov
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

12. 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 974
AED 1,853 total
includes taxes & fees
9 Nov - 10 Nov
Wintergreen cabin, 5 min to ski, hot tub, sauna

13. 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 1,377
AED 3,287 total
includes taxes & fees
3 Dec - 4 Dec
Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort

14. 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

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. Family-Friendly Meets Luxury

Family-Friendly Meets Luxury
Pedlars Edge
9.4 out of 10, Exceptional, (12 reviews)
"Great Spot for Family gathering"
United States
Ary S.
The price is AED 2,088
AED 4,317 total
includes taxes & fees
23 Nov - 24 Nov
Family-Friendly Meets Luxury

17. Designer Home w/ Incredible Views, Sleeps 16

Designer Home w/ Incredible Views, Sleeps 16
Wintergreen Resort
9.4 out of 10, Exceptional, (23 reviews)
"Beautiful property, Beautiful views! Great set up for multiple adults or multiple families/multi-generational gatherings. We had six adults and there were six bedrooms with comfortable beds. The tables have enough seats for everyone in a large group, indoor and outdoor. It’s a private location. It was worth getting up at 6:00 to watch the sunrise. Sauna and Hot tub are a great bonus."
United States
Helen B.
The price is AED 2,088
AED 4,201 total
includes taxes & fees
23 Nov - 24 Nov
Designer Home w/ Incredible Views, Sleeps 16

18. 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 2,105
AED 3,518 total
includes taxes & fees
28 Nov - 29 Nov
Adventure Awaits

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.
The price is AED 2,819
AED 4,444 total
includes taxes & fees
12 Nov - 13 Nov
Privacy and Views in Wintergreen

20. Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"The views and accommodations were awesome. We had such a good time with out family of 14. Plenty to do and plenty of space."
United States
Donna C.
The price is AED 4,594
AED 7,370 total
includes taxes & fees
28 Nov - 29 Nov
Wintergreen Luxury, Breathtaking Views
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.
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Top Wintergreen Hotel Reviews