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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Wintergreen vacation 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 AED 476
AED 1,318 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 560
AED 1,486 total
includes taxes & fees
18 Aug - 19 Aug
The Distinguished Squirrel Chalet walking distance
Exterior

3. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AED 1,084
AED 2,042 total
includes taxes & fees
1 Sep - 2 Sep
Mountain Mindset
Smart TV, fireplace, books

4. 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.
Spacious + Serene Mtn Top Escape, 4 En Suites
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 AED 962
AED 2,017 total
includes taxes & fees
16 Sep - 17 Sep
"Glass & Pine" Home close to Bold Rock & Vineyards
Terrace/patio

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 AED 700
AED 1,791 total
includes taxes & fees
19 Aug - 20 Aug
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Property grounds

7. 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.
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Coffee/tea maker, fridge, microwave, oven

8. 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 AED 1,488
AED 2,805 total
includes taxes & fees
18 Aug - 19 Aug
Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10
Outdoor spa tub

9. 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.
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
Terrace/patio

10. 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.
The price is AED 1,719
AED 3,737 total
includes taxes & fees
25 Aug - 26 Aug
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
Smart TV, fireplace, table tennis, 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 AED 1,369
AED 3,026 total
includes taxes & fees
24 Aug - 25 Aug
4 BR cabin mins to trails & breweries pets welcome
Terrace/patio

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 AED 1,023
AED 2,846 total
includes taxes & fees
23 Aug - 24 Aug
Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14
House, Private Bathroom (Red White Wintergreen) | Exterior

13. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is AED 1,620
AED 3,263 total
includes taxes & fees
20 Aug - 21 Aug
Red White and Wintergreen
Terrace/patio

14. 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 AED 1,491
AED 2,951 total
includes taxes & fees
22 Aug - 23 Aug
Adventure Awaits
Golf

15. 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 AED 1,510
AED 2,879 total
includes taxes & fees
15 Sep - 16 Sep
The Snow House New Hot Tub Pet Friendly Creek PacMan
Fireplace

16. 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 AED 1,103
AED 1,416 total
includes taxes & fees
15 Sep - 16 Sep
Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia
Coffee/tea maker, fridge, microwave, oven

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

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is AED 1,087
AED 2,339 total
includes taxes & fees
31 Aug - 1 Sep
Mountain Retreat: Year-Round Getaway, Pup Friendly
Outdoor dining

18. 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 AED 1,620
AED 3,729 total
includes taxes & fees
20 Aug - 21 Aug
Red White & WTG: Hot Tub, 5 Bedrooms!
House, Private Bathroom (Art & Soul) | Exterior

19. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is AED 2,571
AED 2,887 total
includes taxes & fees
19 Aug - 20 Aug
Art & Soul
House, Private Bathroom (Tucked Inn: Lower Unit) | Exterior

20. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is AED 367
AED 1,031 total
includes taxes & fees
18 Aug - 19 Aug
Tucked Inn: Lower Unit
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

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10/10 Excellent
"We had a great stay! This place has all we could need. We were able to cook what we wanted with ease. We appreciated having a real coffee maker and not just a Keurig. Loved that it was pet friendly. I had a question for the owner and received a very quick response which was greatly appreciated. Overall, would recommend!"
Kim C. 2-night trip
Posted 16 hours ago
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes