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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 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 ￥22,698
￥59,207 total
includes taxes & fees
Nov 16 - Nov 17
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.
The price is ￥33,895
￥75,581 total
includes taxes & fees
Nov 16 - Nov 17
"Glass & Pine" Home close to Bold Rock & Vineyards
A room with a coffee maker, a lamp, and a framed picture on the wall.

4. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
The price is ￥34,764
￥84,678 total
includes taxes & fees
Nov 16 - Nov 17
Walk to SKi Slopes and Hot Tub
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

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 ￥34,938
￥79,029 total
includes taxes & fees
Nov 17 - Nov 18
The Distinguished Squirrel Chalet walking distance
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 ￥33,990
￥96,910 total
includes taxes & fees
Oct 18 - Oct 19
4 BR cabin mins to trails & breweries pets welcome
A modern bathroom with a black vanity, a flat-screen TV mounted above it, and a window with a white curtain.

7. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is ￥61,470
￥135,578 total
includes taxes & fees
Oct 20 - Oct 21
Blackrock Canopy
A deck with outdoor furniture, a table, and a view of the surrounding nature.

8. Merryland with Wintergreen Advantage

Merryland with Wintergreen Advantage
Wintergreen
The price is ￥34,606
￥80,539 total
includes taxes & fees
Nov 1 - Nov 2
Merryland with Wintergreen Advantage
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

9. 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 ￥34,132
￥86,901 total
includes taxes & fees
Nov 4 - Nov 5
Adventure Awaits
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.
The price is ￥56,887
￥136,464 total
includes taxes & fees
Nov 4 - Nov 5
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
A modern kitchen with wooden cabinets, stainless steel appliances, and a wooden dining table with chairs.

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

Wintergreen Resort, Hot Tub, Trails, and Ski!
Nellysford
The price is ￥45,826
￥104,848 total
includes taxes & fees
Nov 11 - Nov 12
Wintergreen Resort, Hot Tub, Trails, and Ski!
A golf course with a mountain backdrop and autumn foliage.

12. 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 ￥47,927
￥101,379 total
includes taxes & fees
Oct 29 - Oct 30
The Snow House New Hot Tub Pet Friendly Creek PacMan
A hot tub with a view of a forested landscape.

13. Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (19 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
The price is ￥53,645
￥124,658 total
includes taxes & fees
Oct 21 - Oct 22
Stunning Views, Hot Tub, Impeccable Design
A cozy living room with a fireplace, a sofa, a coffee table, and a view of the outdoors.

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

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
The price is ￥61,470
￥151,017 total
includes taxes & fees
Oct 19 - Oct 20
Blackrock Canopy: Walk to Ski + 2 Living Spaces
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)
"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 ￥41,951
￥83,867 total
includes taxes & fees
Oct 18 - Oct 19
Wintergreen cabin, 5 min to ski, hot tub, sauna
A cabin with a deck, outdoor seating, and a fire pit.

16. 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 ￥42,849
￥92,045 total
includes taxes & fees
Oct 18 - Oct 19
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A wooden deck with outdoor seating and a fire pit.

17. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ￥54,792
￥97,023 total
includes taxes & fees
Nov 16 - Nov 17
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, (72 reviews)
"Fantastic stay in an amazing property. Wonderful for families with kids of all ages including teens."
United States
Michael R.
The price is ￥73,953
￥154,742 total
includes taxes & fees
Oct 20 - Oct 21
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
A hot tub on a wooden deck with outdoor seating and a view of trees.

19. Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Hilltop Hideaway - Wintergreen 5BR with Hot Tub
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great stay!"
United States
Alyssa C.
The price is ￥73,953
￥160,776 total
includes taxes & fees
Oct 18 - Oct 19
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
A hot tub area with wooden deck, wicker chairs, and a glass door leading to a sauna.

20. Upscale and Family-Friendly in Wintergreen

Upscale and Family-Friendly in Wintergreen
Roseland
9.6 out of 10, Exceptional, (40 reviews)
"Really nice place with a ton of amenities definitely recommend this place to anybody looking for a sweet getaway"
United States
Brian Z.
The price is ￥73,953
￥158,288 total
includes taxes & fees
Oct 25 - Oct 26
Upscale and Family-Friendly in Wintergreen
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

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

10/10 Excellent
"The place was great."
James J. 2-night trip
Posted 1 day ago
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
315
Accommodation
210 Vacation Homes
Lowest Price
￥59,207
Highest Price
￥160,776

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