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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (56 reviews)
"Great place"
United States
Stephen M.
The price is ￥15,320
￥60,649 total
includes taxes & fees
Sep 1 - Sep 2
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, (32 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is ￥20,632
￥57,138 total
includes taxes & fees
Aug 31 - Sep 1
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, (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.
The price is ￥29,025
￥69,333 total
includes taxes & fees
Sep 1 - Sep 2
"Glass & Pine" Home close to Bold Rock & Vineyards
A wooden deck with outdoor seating and a fire pit.

4. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ￥45,690
￥87,066 total
includes taxes & fees
Sep 9 - Sep 10
Mountain Mindset
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, (35 reviews)
"it is really excellent."
United States
RK D.
The price is ￥30,819
￥94,530 total
includes taxes & fees
Aug 28 - Aug 29
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.
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

7. The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.2 out of 10, Wonderful, (13 reviews)
"Great location and the slopes are easily accessible!"
United States
Mark H.
The price is ￥37,667
￥83,637 total
includes taxes & fees
Sep 14 - Sep 15
The Distinguished Squirrel Chalet walking distance
A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

8. 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 ￥57,337
￥138,974 total
includes taxes & fees
Sep 8 - Sep 9
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

9. Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia

Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia
Wintergreen Resort
The price is ￥36,791
￥47,040 total
includes taxes & fees
Sep 10 - Sep 11
Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia
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 ￥51,317
￥106,815 total
includes taxes & fees
Sep 2 - Sep 3
The Snow House New Hot Tub Pet Friendly Creek PacMan
A hot tub with a view of a forest.

11. 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)
"Fabulous house and we all had a great time! "
United States
Mindy M.
The price is ￥55,580
￥154,846 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
A two-story cabin with a deck, large windows, and a hot tub.

12. 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 ￥44,341
￥123,420 total
includes taxes & fees
Sep 3 - Sep 4
Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14

13. Sunset Views, Hot Tub, and Firepit in Wintergreen!

Sunset Views, Hot Tub, and Firepit in Wintergreen!
Wintergreen Resort
The price is ￥111,808
￥199,959 total
includes taxes & fees
Sep 3 - Sep 4
Sunset Views, Hot Tub, and Firepit in Wintergreen!
A two-story stone house with a deck, outdoor seating, and a fireplace.

14. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is ￥60,363
￥130,389 total
includes taxes & fees
Aug 30 - Aug 31
Red White and Wintergreen
A two-story house with a deck, hot tub, and outdoor seating area.

15. Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Wintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
"Everything was perfect! The host was extremely responsive and the property was in excellent condition "
United States
liz b.
Wintergreen Luxury, Breathtaking Views

16. Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is ￥45,850
￥99,760 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Retreat: Year-Round Getaway, Pup Friendly
A bunk bed room with a red and white chevron rug, a white door, and a red dresser.

17. Red White & WTG: Hot Tub, 5 Bedrooms!

Red White & WTG: Hot Tub, 5 Bedrooms!
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"House was perfection. Very comfortable beds and every comfort of home is available in this property. Perfect place for two families of four to enjoy a fun weekend on the mountain. "
United States
Kate T.
The price is ￥60,363
￥148,990 total
includes taxes & fees
Aug 30 - Aug 31
Red White & WTG: Hot Tub, 5 Bedrooms!

18. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is ￥111,440
￥125,147 total
includes taxes & fees
Sep 1 - Sep 2
Art & Soul
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

19. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is ￥15,920
￥44,695 total
includes taxes & fees
Sep 1 - Sep 2
Tucked Inn: Lower Unit
A wooden cabin with a sloped roof, a front porch, and a pathway leading to the entrance.

20. Blue's Barn: Central to Wineries & Breweries

Blue's Barn: Central to Wineries & Breweries
Nellysford
9.6 out of 10, Exceptional, (22 reviews)
"A great location and comfortable stay! The unit was extremely clean, great communication from the host, we enjoyed the outdoor fire pit and how central it was to dining and outings in the area."
United States
Sarah N.
The price is ￥25,324
￥49,904 total
includes taxes & fees
Aug 28 - Aug 29
Blue's Barn: Central to Wineries & Breweries
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

Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

10/10 Excellent
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
Shannon T. 2-night trip
Posted 2 days ago
Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
198
Accommodation
210 Vacation Homes
Lowest Price
￥44,695
Highest Price
￥199,959

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