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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Wintergreen holiday homes

Exterior

1. 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 £262
includes taxes & fees
31 Aug - 1 Sept
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
TV, fireplace, offices

2. 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 £308
includes taxes & fees
18 Aug - 19 Aug
The Distinguished Squirrel Chalet walking distance
Smart TV, fireplace, books

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, (56 reviews)
"Great place"
United States
Stephen M.
The price is £295
includes taxes & fees
15 Aug - 16 Aug
Spacious + Serene Mtn Top Escape, 4 En Suites
Pool

4. Relaxing Wintergreen Chalet

Relaxing Wintergreen Chalet
Chestnut Springs
8.0 out of 10, Very good, (21 reviews)
"Enjoyed our stay and the owner was very helpful and informative."
United States
richard r.
The price is £336
includes taxes & fees
15 Aug - 16 Aug
Relaxing Wintergreen Chalet
Dining

5. "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 £364
includes taxes & fees
13 Sept - 14 Sept
"Glass & Pine" Home close to Bold Rock & Vineyards
Exterior

6. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is £420
includes taxes & fees
31 Aug - 1 Sept
Mountain Mindset
Outdoor dining

7. Wintergreen cabin, hot tub, sauna, walk to trails

Wintergreen cabin, hot tub, sauna, walk to trails
Chestnut Springs
10.0 out of 10, Exceptional, (9 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 £358
includes taxes & fees
16 Aug - 17 Aug
Wintergreen cabin, hot tub, sauna, walk to trails
Terrace/patio

8. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.4 out of 10, Exceptional, (9 reviews)
"Holly was amazing! We loved the location, the coziness, and the house had all the bells and whistles! Adventure Awaits made our Wintergreen vacation the best! "
United States
Kimberly K.
The price is £537
includes taxes & fees
22 Aug - 23 Aug
Adventure Awaits
Property grounds

9. 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 £656
includes taxes & fees
8 Sept - 9 Sept
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Outdoor spa tub

10. 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 £729
includes taxes & fees
26 Aug - 27 Aug
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
Smart TV, fireplace, ping pong, books

11. 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)
"We really enjoyed our stay in Wintergreen! The location was great and the view was incredible. The house was spotless and we loved that there was a full kitchen. We recommend to others! "
United States
Laura J.
The price is £440
includes taxes & fees
14 Aug - 15 Aug
4 BR cabin mins to trails & breweries pets welcome
Coffee/tea maker, fridge, microwave, oven

12. Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10

Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10
Pedlars Edge
10.0 out of 10, Exceptional, (6 reviews)
"Great location and nice home!"
United States
Hesham A.
The price is £572
includes taxes & fees
14 Aug - 15 Aug
Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10
Terrace/patio

13. 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 £561
includes taxes & fees
20 Aug - 21 Aug
Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14
Golf

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 price is £550
includes taxes & fees
24 Aug - 25 Aug
The Snow House New Hot Tub Pet Friendly Creek PacMan
Interior

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

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is £480
includes taxes & fees
1 Sept - 2 Sept
Mountain Retreat: Year-Round Getaway, Pup Friendly
House, Private Bathroom (Red White Wintergreen) | Exterior

16. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
Red White and Wintergreen
TV, fireplace, video games, computer monitors

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.
Red White & WTG: Hot Tub, 5 Bedrooms!
House, Private Bathroom (Art & Soul) | Exterior

18. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is £582
includes taxes & fees
16 Aug - 17 Aug
Art & Soul
House, Private Bathroom (Tucked Inn: Upper Unit) | Terrace/patio

19. Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is £212
includes taxes & fees
16 Aug - 17 Aug
Tucked Inn: Upper Unit
Interior

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 £232
includes taxes & fees
16 Aug - 17 Aug
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

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

10/10 Excellent
"Great communication with the host and the view of the mountains was spectacular"
Erik H. 1-night trip
Posted 7 hours ago
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews
223
Accommodation
211 Holiday Homes
Lowest Price
£212
Highest Price
£729