Wintergreen, VA Vacation Homes from ￥60,313

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

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Our top choices for Wintergreen vacation 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!

Wintergreen Resort

Stanley W.

￥60,313 total

includes taxes & fees

Oct 7 - Oct 8

A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

2. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

￥69,600 total

includes taxes & fees

Oct 5 - Oct 6

A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

3. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

￥92,480 total

includes taxes & fees

Oct 6 - Oct 7

A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

4. Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort

Maija

A modern kitchen with wooden beams, a large island, and a dining area with a bench.

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

Nellysford

Robert H.

￥73,561 total

includes taxes & fees

Oct 1 - Oct 2

A cabin with a deck, outdoor seating, and a fire pit.

6. Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Chestnut Springs

Cheryl P.

￥100,188 total

includes taxes & fees

Oct 4 - Oct 5

A room with a coffee maker, a lamp, and a framed picture on the wall.

7. Walk to SKi Slopes and Hot Tub

Treeloft

￥83,727 total

includes taxes & fees

Oct 12 - Oct 13

A spacious living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

8. Private Mountain Getaway Wintergreen Resort

Chestnut Springs

￥97,025 total

includes taxes & fees

Oct 5 - Oct 6

A two-story stone house with a deck, outdoor seating, and a fireplace.

9. Red White and Wintergreen

Pedlars Edge

￥135,726 total

includes taxes & fees

Oct 4 - Oct 5

A deck with a fire pit, outdoor furniture, and a view of trees and a sunset.

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

Chestnut Springs

mikenzi b.

A bedroom with a bed, a wooden headboard, a large wall clock, and a view of a hallway.

11. Merryland with Wintergreen Advantage

Wintergreen

￥93,462 total

includes taxes & fees

Oct 5 - Oct 6

A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

12. Adventure Awaits

Laurel Ridge

Kimberly K.

￥100,450 total

includes taxes & fees

Oct 27 - Oct 28

13. Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Laurel Ridge

Mindy M.

￥153,066 total

includes taxes & fees

Oct 5 - Oct 6

A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

14. Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Nellysford

Rachel F.

￥152,515 total

includes taxes & fees

Oct 5 - Oct 6

A golf course with a mountain backdrop and autumn foliage.

15. The Snow House New Hot Tub Pet Friendly Creek PacMan

Wintergreen Resort

Justin L.

￥93,665 total

includes taxes & fees

Oct 14 - Oct 15

A two-story cabin with a deck, large windows, and a hot tub.

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

Wintergreen Resort

"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...

Paula L.

￥116,223 total

includes taxes & fees

Oct 7 - Oct 8