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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 AU$525
includes taxes & fees
9 Nov - 10 Nov
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.

2. "Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Great house and location near lots of activities. The home was very clean and the kitchen was well stocked. Very nice to sit and relax on the deck. The host was quick to respond to any questions and communication was great. Definitely recommend if you are looking to stay somewhere along 151 or near Wintergreen."
United States
Dean G.
"Glass & Pine" Home close to Bold Rock & Vineyards
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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, (61 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
The price is AU$579
includes taxes & fees
18 Oct - 19 Oct
Spacious + Serene Mtn Top Escape, 4 En Suites
A room with a coffee maker, a lamp, and a framed picture on the wall.

4. Walk to SKi Slopes and Hot Tub

Walk to SKi Slopes and Hot Tub
Treeloft
The price is AU$755
includes taxes & fees
3 Nov - 4 Nov
Walk to SKi Slopes and Hot Tub
A modern bathroom with a black vanity, a flat-screen TV mounted above it, and a window with a white curtain.

5. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is AU$1,229
includes taxes & fees
28 Oct - 29 Oct
Blackrock Canopy
A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

6. 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 AU$843
includes taxes & fees
3 Nov - 4 Nov
4 BR cabin mins to trails & breweries pets welcome
A deck with outdoor furniture, a table, and a view of the surrounding nature.

7. Merryland with Wintergreen Advantage

Merryland with Wintergreen Advantage
Wintergreen
The price is AU$712
includes taxes & fees
1 Nov - 2 Nov
Merryland with Wintergreen Advantage
A pendant light fixture with a geometric design.

8. 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 AU$676
includes taxes & fees
27 Oct - 28 Oct
The Distinguished Squirrel Chalet walking distance
A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

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 AU$1,222
includes taxes & fees
3 Nov - 4 Nov
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
A modern kitchen with wooden cabinets, stainless steel appliances, and a wooden dining table with chairs.

10. Wintergreen Resort, Hot Tub, Trails, and Ski!

Wintergreen Resort, Hot Tub, Trails, and Ski!
Nellysford
Wintergreen Resort, Hot Tub, Trails, and Ski!
A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

11. Adventure Awaits

Adventure Awaits
Laurel Ridge
9.0 out of 10, Wonderful, (10 reviews)
"our stay was so fun! "
United States
Kaden C.
The price is AU$796
includes taxes & fees
3 Nov - 4 Nov
Adventure Awaits
A two-story cabin with a deck, large windows, and a hot tub.

12. 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.
Fall Getaway | Sauna & Hot Tub | Sleeps 14
A spacious living area with a stone fireplace, large windows, and a high ceiling with exposed wood beams.

13. Trail Magic- Sk-in & Ski-out

Trail Magic- Sk-in & Ski-out
Treeloft
10.0 out of 10, Exceptional, (5 reviews)
"Great place!"
United States
Robert P.
The price is AU$1,140
includes taxes & fees
15 Nov - 16 Nov
Trail Magic- Sk-in & Ski-out
A golf course with a mountain backdrop and autumn foliage.

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, (11 reviews)
"Great time, great location and very smooth process. Looking forward to planning another stay next ski season. "
United States
Justin L.
The Snow House New Hot Tub Pet Friendly Creek PacMan
A wooden deck with outdoor seating and a fire pit.

15. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AU$950
includes taxes & fees
3 Nov - 4 Nov
Mountain Mindset
A cozy living room with a fireplace, a sofa, a coffee table, and a view of the outdoors.

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

Blackrock Canopy: Walk to Ski + 2 Living Spaces
Wintergreen Resort
Blackrock Canopy: Walk to Ski + 2 Living Spaces
A deck with a fire pit, outdoor furniture, and a view of trees and a sunset.

17. Wintergreen cabin, 5 min to ski, hot tub, sauna

Wintergreen cabin, 5 min to ski, hot tub, sauna
Chestnut Springs
10.0 out of 10, Exceptional, (16 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 AU$833
includes taxes & fees
4 Nov - 5 Nov
Wintergreen cabin, 5 min to ski, hot tub, sauna
A hot tub with a view of a forested landscape.

18. Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (18 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
The price is AU$1,104
includes taxes & fees
21 Oct - 22 Oct
Stunning Views, Hot Tub, Impeccable Design
A hot tub on a wooden deck with outdoor seating and a view of trees.

19. 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.
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
A cabin with a deck, outdoor seating, and a fire pit.

20. 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, (20 reviews)
"Great stay!"
United States
Cheryl P.
The price is AU$901
includes taxes & fees
18 Oct - 19 Oct
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
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

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent
"Beautiful views with all the necessary amenities. Maureen, the host, was always responsive to our questions and communication was excellent."
Alan B. 2-night trip
Posted 15 hours ago
Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews
189
Accommodation
217 Holiday Homes
Lowest Price
AU$525
Highest Price
AU$1,229