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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Wintergreen vacation homes

A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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, (60 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
Spacious + Serene Mtn Top Escape, 4 En Suites
A cabin with a large window, surrounded by trees.

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, (35 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A modern kitchen with wooden beams, a large island, and a dining area with a bench.

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.
"Glass & Pine" Home close to Bold Rock & Vineyards
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

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 929
AED 1,989 total
includes taxes & fees
9 Nov - 10 Nov
The Distinguished Squirrel Chalet walking distance
A room with a coffee maker, a lamp, and a framed picture on the wall.

5. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
The price is AED 790
AED 1,935 total
includes taxes & fees
3 Nov - 4 Nov
Walk to SKi Slopes and Hot Tub
A modern bathroom with a black vanity, a flat-screen TV mounted above it, and a window with a white curtain.

6. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
Blackrock Canopy
A deck with outdoor furniture, a table, and a view of the surrounding nature.

7. Merryland with Wintergreen Advantage

Merryland with Wintergreen Advantage
Wintergreen
Merryland with Wintergreen Advantage
A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

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, (36 reviews)
"it is really excellent."
United States
RK D.
The price is AED 826
AED 2,314 total
includes taxes & fees
12 Oct - 13 Oct
4 BR cabin mins to trails & breweries pets welcome
A golf course with a mountain backdrop and autumn foliage.

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, (10 reviews)
"Great time, great location and very smooth process. Looking forward to planning another stay next ski season. "
United States
Justin L.
The Snow House New Hot Tub Pet Friendly Creek PacMan
A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

10. 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.
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
A two-story cabin with a deck, large windows, and a hot tub.

11. 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 1,304
AED 3,214 total
includes taxes & fees
19 Oct - 20 Oct
Fall Getaway | Sauna & Hot Tub | Sleeps 14
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

12. 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 1,994
AED 3,571 total
includes taxes & fees
23 Oct - 24 Oct
Adventure Awaits
A spacious living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

13. Private Mountain Getaway Wintergreen Resort

Private Mountain Getaway Wintergreen Resort
Chestnut Springs
The price is AED 1,164
AED 2,586 total
includes taxes & fees
14 Oct - 15 Oct
Private Mountain Getaway Wintergreen Resort
A hot tub with a view of a forested landscape.

14. Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (18 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
Stunning Views, Hot Tub, Impeccable Design
A spacious living area with a stone fireplace, large windows, and a high ceiling with exposed wood beams.

15. Trail Magic- Sk-in & Ski-out

Trail Magic- Sk-in & Ski-out
Treeloft
10.0 out of 10, Exceptional, (5 reviews)
"Great place!"
United States
Robert P.
The price is AED 1,392
AED 3,304 total
includes taxes & fees
14 Oct - 15 Oct
Trail Magic- Sk-in & Ski-out
A wooden deck with outdoor seating and a fire pit.

16. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AED 1,190
AED 2,161 total
includes taxes & fees
3 Nov - 4 Nov
Mountain Mindset
A cabin with a deck, outdoor seating, and a fire pit.

17. 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
A cozy living room with a fireplace, a sofa, a coffee table, and a view of the outdoors.

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

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
Blackrock Canopy: Walk to Ski + 2 Living Spaces
A two-story house with a central entrance, a wooden staircase, and a porch.

19. Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Wintergreen Resort
10.0 out of 10, Exceptional, (71 reviews)
"Fantastic stay in an amazing property. Wonderful for families with kids of all ages including teens."
United States
Michael R.
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
A spacious living room with a fireplace, large windows, and a stone accent wall.

20. Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!

Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!
Pedlars Edge
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay! House was clean and comfortable. The kids really enjoyed the downstairs space and the adults the outside space!"
United States
Lisa D.
Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!
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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

10/10 Excellent
"Beautiful place, has everything you can imagine, the view is also amazing, 100% recommended."
Monica C. 3-night trip
Posted 2 days ago
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14