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Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (61 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
Spacious + Serene Mtn Top Escape, 4 En Suites
A modern living room with a large flat-screen TV, a brown leather sofa, a wooden coffee table, and a large window with a view of trees.

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.
3 mins to skiing! Cozy chalet w/ king beds, fireplace, & hot tub. 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, (4 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 Distinguished Squirrel Chalet walking distance
A kitchen with wooden cabinets, a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

5. Mountaintop Wintergreen Resort Home w/ Deck, Views

Mountaintop Wintergreen Resort Home w/ Deck, Views
Wintergreen Resort
9.8 out of 10, Exceptional, (62 reviews)
"Great stay and great communication. Well worth the price for the stay."
United States
Todd A.
Mountaintop Wintergreen Resort Home w/ Deck, Views
A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

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.
4 BR cabin mins to trails & breweries pets welcome
A two-story cabin with a balcony, surrounded by trees.

7. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
Blackrock Canopy
A cabin with a deck, outdoor seating, and a fire pit.

8. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
Walk to SKi Slopes and Hot Tub
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, (11 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 cabin with a deck, outdoor seating, and a fire pit.

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
A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

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.
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
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.
Adventure Awaits
A two-story cabin with a balcony, surrounded by trees.

13. 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 deck with outdoor furniture, a fire pit, and string lights.

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
A deck with a fire pit, outdoor furniture, and a view of trees and a sunset.

15. 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)
"We loved our stay at this property. The place was perfect for a family of 4 and we loved that we could bring our dogs. Beautifully decorated and a great deck out back for relaxing with in what felt like a treehouse. Would definitely go back"
United States
Dan S.
Wintergreen cabin, 5 min to ski, hot tub, sauna
A residential property with a patio area, outdoor seating, a hot tub, and a fire pit.

16. 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 Black Walnut - Your Own Private Resort
A wooden deck with outdoor seating and a fire pit.

17. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
Mountain Mindset
A two-story house with a central entrance, a wooden staircase, and a porch.

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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Wintergreen Resort
10.0 out of 10, Exceptional, (73 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 large windows, a wooden ceiling, and a chandelier.

19. Designer Home w/ Incredible Views, Sleeps 16

Designer Home w/ Incredible Views, Sleeps 16
Wintergreen Resort
9.4 out of 10, Exceptional, (23 reviews)
"We enjoyed our stay at this beautiful place. love to come back "
United States
Neda A.
Designer Home w/ Incredible Views, Sleeps 16
A cozy outdoor seating area with a fire pit, wooden deck, and a large wooden barrel.

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.
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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.

See all hotels in Wintergreen
A mountainous landscape with lush green hills and a clear blue sky with contrails.

Top reviews in Wintergreen

A hallway with a wooden staircase, a bench, and a door leading to a balcony.
Fore Seasons

Fore Seasons

Fore Seasons
Nellysford

10/10 Excellent

Me and my family had such a great time. The house was clean and beautiful. Everything about the house was amazing. The hosts were very responsive and sincere.❤️
United States
Menen
Reviewed September 7, 2026
Fore Seasons

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