A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Holiday Homes in Wintergreen

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Check prices for these dates

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

Our top choices for Wintergreen holiday homes

Smart TV, fireplace, books

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 NZ$623
includes taxes & fees
30 Aug - 31 Aug
Spacious + Serene Mtn Top Escape, 4 En Suites
Exterior

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 NZ$588
includes taxes & fees
31 Aug - 1 Sept
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Dining

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 NZ$727
includes taxes & fees
1 Sept - 2 Sept
"Glass & Pine" Home close to Bold Rock & Vineyards
Smart TV, fireplace, ping pong, books

4. 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 NZ$960
includes taxes & fees
9 Sept - 10 Sept
4 BR cabin mins to trails & breweries pets welcome
Exterior

5. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is NZ$885
includes taxes & fees
30 Aug - 31 Aug
Mountain Mindset
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.
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
TV, fireplace, offices

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 NZ$844
includes taxes & fees
14 Sept - 15 Sept
The Distinguished Squirrel Chalet walking distance
Fireplace

8. 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 NZ$492
includes taxes & fees
10 Sept - 11 Sept
Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia
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 NZ$1,405
includes taxes & fees
8 Sept - 9 Sept
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Outdoor spa tub

10. 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 NZ$1,160
includes taxes & fees
28 Sept - 29 Sept
Stunning Views, Hot Tub, Impeccable Design
Golf

11. 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 NZ$1,069
includes taxes & fees
1 Sept - 2 Sept
The Snow House New Hot Tub Pet Friendly Creek PacMan
Outdoor spa tub

12. 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 NZ$1,585
includes taxes & fees
31 Aug - 1 Sept
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
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 NZ$1,295
includes taxes & fees
7 Sept - 8 Sept
Sauna & Hot Tub - 7th Hole Chalet - Sleeps 14
House, Private Bathroom (Red White Wintergreen) | Exterior

14. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is NZ$1,384
includes taxes & fees
30 Aug - 31 Aug
Red White and Wintergreen
Smart TV, video games, table football

15. 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.
The price is NZ$1,918
includes taxes & fees
27 Sept - 28 Sept
Designer Home w/ Incredible Views, Sleeps 16
Coffee/tea maker, fridge, microwave, oven

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

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is NZ$1,018
includes taxes & fees
9 Sept - 10 Sept
Mountain Retreat: Year-Round Getaway, Pup Friendly
5 bedrooms, desk, iron/ironing board, free WiFi

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 NZ$1,329
includes taxes & fees
30 Aug - 31 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 NZ$484
includes taxes & fees
30 Aug - 31 Aug
Tucked Inn: Upper 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

Newly Built Designer Home in Wintergreen

Newly Built Designer Home in Wintergreen

10/10 Excellent
"This is one of the finest properties we've ever visited in all of our trips to Wintergreen. We have been coming since 1978. The location is great. It's snuggled into the lower elevations of the resort. That will pay dividends during your stay. Less vehicular and foot traffic. Combine that with easy access to the Appalachian Trail for some of the best hiking and views in the Blue Ridge. Ideal for kids and pets.The property itself? Beautiful, clean, tasteful, accommodating. The lighting and furnishings are designer quality. The well stocked kitchen is a joy to use with all of the necessary gadgets and utensils. Prefer pour over coffee? Your goose neck kettle is waiting. More of a French press kind of person? The Fellow Clara press is ready to go.The bedrooms and bathrooms are beautifully appointed. The wifi and entertainment setup are top drawer. You will not be disappointed. Highly recommended!"
Michael L. 7-night trip
Posted 1 day ago
Newly Built Designer Home in Wintergreen

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews
205
Accommodation
209 Holiday Homes
Lowest Price
NZ$484
Highest Price
NZ$1,918

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