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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (59 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
The price is ￥16,360
￥58,650 total
includes taxes & fees
Sep 24 - Sep 25
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 ￥20,406
￥56,157 total
includes taxes & fees
Sep 28 - Sep 29
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

3. 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 ￥28,706
￥69,635 total
includes taxes & fees
Sep 30 - Oct 1
The Distinguished Squirrel Chalet walking distance
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, (2 reviews)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
"Glass & Pine" Home close to Bold Rock & Vineyards
A spacious living room with a stone fireplace, a wooden ceiling, and large windows offering a view of trees.

5. 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 ￥30,750
￥92,527 total
includes taxes & fees
Sep 27 - Sep 28
4 BR cabin mins to trails & breweries pets welcome
A cabin with a deck, outdoor seating, and a fire pit.

6. 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, (18 reviews)
"Great stay!"
United States
Cheryl P.
The price is ￥34,636
￥78,952 total
includes taxes & fees
Sep 24 - Sep 25
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A two-story stone house with a deck, outdoor seating, and a fireplace.

7. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is ￥59,620
￥128,784 total
includes taxes & fees
Sep 24 - Sep 25
Red White and Wintergreen
A modern kitchen with white cabinetry, stainless steel appliances, and a large window.

8. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
Walk to SKi Slopes and Hot Tub
A hot tub with a view of a forested landscape.

9. Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (17 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
The price is ￥40,902
￥107,996 total
includes taxes & fees
Sep 28 - Sep 29
Stunning Views, Hot Tub, Impeccable Design
A golf course with a mountain backdrop and autumn foliage.

10. 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 price is ￥44,779
￥93,429 total
includes taxes & fees
Sep 24 - Sep 25
The Snow House New Hot Tub Pet Friendly Creek PacMan
A two-story cabin with a deck, large windows, and a hot tub.

11. Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14

Sauna & Hot Tub - 7th Hole Chalet - 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 ￥30,684
￥100,233 total
includes taxes & fees
Sep 24 - Sep 25
Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14
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)
The price is ￥71,010
￥155,775 total
includes taxes & fees
Sep 28 - Sep 29
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
A hot tub with a view of a forest.

13. Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
Laurel Ridge
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥54,969
￥153,144 total
includes taxes & fees
Sep 28 - Sep 29
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
A spacious living room with a fireplace, large windows, and a stone accent wall.

14. 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, (1 review)
"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!
A spacious kitchen with a central island, a stone fireplace, and a dining area with a high ceiling and wooden beams.

15. Luxury Oasis! Ski, Hike, Brew Trails, Winter Fun. Hot Tub. Firepit. Pet friendly

Luxury Oasis! Ski, Hike, Brew Trails, Winter Fun. Hot Tub. Firepit. Pet friendly
Chestnut Springs
10.0 out of 10, Exceptional, (13 reviews)
The price is ￥73,687
￥170,275 total
includes taxes & fees
Oct 4 - Oct 5
Luxury Oasis! Ski, Hike, Brew Trails, Winter Fun. Hot Tub. Firepit. Pet friendly
A spacious living room with large windows, a wooden ceiling, and a chandelier.

16. 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 wooden deck with outdoor seating and a fire pit.

17. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ￥58,571
￥101,139 total
includes taxes & fees
Sep 24 - Sep 25
Mountain Mindset
A hot tub on a wooden deck with outdoor seating and a view of trees.

18. 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 spacious living area with a stone fireplace, large windows, and a high ceiling with exposed wood beams.

19. 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 ￥122,230
￥223,579 total
includes taxes & fees
Oct 11 - Oct 12
Trail Magic- Sk-in & Ski-out
A two-story house with a deck, hot tub, and outdoor seating area.

20. Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Everything was perfect! The host was extremely responsive and the property was in excellent condition "
United States
liz b.
The price is ￥114,522
￥226,654 total
includes taxes & fees
Oct 12 - Oct 13
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

Your Mountain Cabin Getaway Awaits!

Your Mountain Cabin Getaway Awaits!

10/10 Excellent
"The house was just like the photos and descriptions. It turned out to be a great property, near the hiking trails, full of charm, well decorated, lots of space for a group and overall really enjoyed our time there."
Chris M. 2-night trip
Posted 2 days ago
Your Mountain Cabin Getaway Awaits!

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
209
Accommodation
210 Vacation Homes
Lowest Price
￥56,157
Highest Price
￥226,654

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