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

Our top choices for Wintergreen vacation homes

A deck with outdoor furniture, a fire pit, and a covered area with sliding glass doors.

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

Wintergreen Resort, Hot Tub, Trails, and Ski!
Nellysford
Wintergreen Resort, Hot Tub, Trails, and Ski!
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.
The price is ￥23,424
￥59,728 total
includes taxes & fees
Nov 9 - Nov 10
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

3. 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
The price is ￥26,313
￥73,994 total
includes taxes & fees
Oct 14 - Oct 15
Spacious + Serene Mtn Top Escape, 4 En Suites
A modern kitchen with wooden beams, a large island, and a dining area with a bench.

4. "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 ￥33,957
￥75,186 total
includes taxes & fees
Nov 9 - Nov 10
"Glass & Pine" Home close to Bold Rock & Vineyards
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 ￥34,037
￥83,412 total
includes taxes & fees
Nov 3 - Nov 4
Walk to SKi Slopes and Hot Tub
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, (36 reviews)
"it is really excellent."
United States
RK D.
The price is ￥33,087
￥95,824 total
includes taxes & fees
Nov 3 - Nov 4
4 BR cabin mins to trails & breweries pets welcome
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 wooden deck with outdoor seating and a fire pit.

8. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ￥49,709
￥91,379 total
includes taxes & fees
Nov 9 - Nov 10
Mountain Mindset
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

9. 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 ￥38,833
￥84,710 total
includes taxes & fees
Nov 10 - Nov 11
The Distinguished Squirrel Chalet walking distance
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

10. 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 ￥37,045
￥89,905 total
includes taxes & fees
Nov 3 - Nov 4
Adventure Awaits
A spacious living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

11. Private Mountain Getaway Wintergreen Resort

Private Mountain Getaway Wintergreen Resort
Chestnut Springs
The price is ￥42,427
￥99,735 total
includes taxes & fees
Nov 2 - Nov 3
Private Mountain Getaway Wintergreen Resort
A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

12. 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 ￥60,474
￥141,160 total
includes taxes & fees
Oct 28 - Oct 29
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
A spacious living area with a stone fireplace, large windows, and a high ceiling with exposed wood beams.

13. 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 ￥51,767
￥131,923 total
includes taxes & fees
Nov 9 - Nov 10
Trail Magic- Sk-in & Ski-out
A golf course with a mountain backdrop and autumn foliage.

14. 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 two-story cabin with a deck, large windows, and a hot tub.

15. 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 ￥65,946
￥151,096 total
includes taxes & fees
Oct 22 - Oct 23
Fall Getaway | Sauna & Hot Tub | Sleeps 14
A hot tub with a view of a forested landscape.

16. 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 hot tub on a wooden deck with outdoor seating and a view of trees.

17. Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Hilltop Hideaway - Wintergreen 5BR with Hot Tub
Wintergreen Resort
10.0 out of 10, Exceptional, (7 reviews)
"Great stay!"
United States
Alyssa C.
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
A modern bathroom with a black vanity, a flat-screen TV mounted above it, and a window with a white curtain.

18. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is ￥61,583
￥135,827 total
includes taxes & fees
Oct 26 - Oct 27
Blackrock Canopy
A cabin with a deck, outdoor seating, and a fire pit.

19. 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 ￥45,169
￥95,798 total
includes taxes & fees
Oct 12 - Oct 13
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A two-story house with a central entrance, a wooden staircase, and a porch.

20. 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.
The price is ￥74,089
￥155,027 total
includes taxes & fees
Oct 20 - Oct 21
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
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

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
242
Accommodation
210 Vacation Homes
Lowest Price
￥59,728
Highest Price
￥155,027

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