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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wintergreen holiday homes

A cabin with a large window, surrounded by trees.

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, (35 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is £268
includes taxes & fees
29 Sept - 30 Sept
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

2. 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 £275
includes taxes & fees
29 Sept - 30 Sept
Spacious + Serene Mtn Top Escape, 4 En Suites
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 £323
includes taxes & fees
29 Sept - 30 Sept
"Glass & Pine" Home close to Bold Rock & Vineyards
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

4. 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 £395
includes taxes & fees
2 Oct - 3 Oct
The Distinguished Squirrel Chalet walking distance
A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

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 £448
includes taxes & fees
29 Sept - 30 Sept
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, (19 reviews)
"Great stay!"
United States
Cheryl P.
The price is £369
includes taxes & fees
30 Sept - 1 Oct
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
A spacious living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

7. Private Mountain Getaway Wintergreen Resort

Private Mountain Getaway Wintergreen Resort
Chestnut Springs
The price is £496
includes taxes & fees
27 Oct - 28 Oct
Private Mountain Getaway Wintergreen Resort
A room with a coffee maker, a lamp, and a framed picture on the wall.

8. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
Walk to SKi Slopes and Hot Tub
A wooden deck with outdoor seating and a fire pit.

9. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is £448
includes taxes & fees
29 Sept - 30 Sept
Mountain Mindset
A cozy living room with a fireplace, a sofa, a chair, a coffee table, and a bookshelf.

10. Merryland with Wintergreen Advantage

Merryland with Wintergreen Advantage
Wintergreen
The price is £451
includes taxes & fees
12 Oct - 13 Oct
Merryland with Wintergreen Advantage
A hot tub with a view of a forested landscape.

11. 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.
Stunning Views, Hot Tub, Impeccable Design
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)
"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!
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

13. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.0 out of 10, Wonderful, (10 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 £439
includes taxes & fees
29 Sept - 30 Sept
Adventure Awaits
A hot tub with a view of a forest.

14. 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 £728
includes taxes & fees
29 Sept - 30 Sept
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
A two-story cabin with a deck, large windows, and a hot tub.

15. Fall Getaway | Sauna & Hot Tub | Sleeps 14

Fall Getaway | Sauna & Hot Tub | 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 £562
includes taxes & fees
7 Oct - 8 Oct
Fall Getaway | Sauna & Hot Tub | Sleeps 14
A bedroom with a bed, bedside tables, a window with sheer curtains, and a wall-mounted painting.

16. Blackrock Canopy: Walk to Ski + 2 Living Spaces

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
The price is £1,211
includes taxes & fees
2 Oct - 3 Oct
Blackrock Canopy: Walk to Ski + 2 Living Spaces
A spacious living room with large windows, a wooden ceiling, and a chandelier.

17. 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 golf course with a mountain backdrop and autumn foliage.

18. 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 £479
includes taxes & fees
13 Oct - 14 Oct
The Snow House New Hot Tub Pet Friendly Creek PacMan
A two-story stone house with a deck, outdoor seating, and a fireplace.

19. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is £618
includes taxes & fees
29 Sept - 30 Sept
Red White and Wintergreen
A spacious living room with a fireplace, large windows, and a stone accent wall.

20. 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!
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 cabin, hot tub, sauna, walk to trails

Wintergreen cabin, hot tub, sauna, walk to trails

10/10 Excellent
"We loved this place! And will definitely be staying there again :)"
Stephanie A. 2-night trip
Posted 16 hours ago
Wintergreen cabin, hot tub, sauna, walk to trails

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews
200
Accommodation
208 Holiday Homes
Lowest Price
£268
Highest Price
£728