Wintergreen, VA Vacation Homes from ￥43,907

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

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

Wintergreen Resort

Dawn

￥57,547 total

includes taxes & fees

Sep 13 - Sep 14

A cabin with a large window, surrounded by trees.

2. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Wintergreen Resort

Stanley W.

￥55,442 total

includes taxes & fees

Sep 17 - Sep 18

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

3. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

￥60,083 total

includes taxes & fees

Sep 14 - Sep 15

A spacious living room with a stone fireplace, a wooden ceiling, and large windows offering a view of trees.

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

Chestnut Springs

RK D.

￥89,793 total

includes taxes & fees

Sep 13 - Sep 14

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.

￥76,562 total

includes taxes & fees

Sep 29 - Sep 30

A modern kitchen with white cabinetry, stainless steel appliances, and a large window.

6. Walk to SKi Slopes and Hot Tub

Treeloft

￥87,771 total

includes taxes & fees

Oct 1 - Oct 2

A wooden deck with outdoor seating and a fire pit.

7. Mountain Mindset

Laurel Ridge

￥93,148 total

includes taxes & fees

Sep 16 - Sep 17

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

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

Nellysford

Rachel F.

￥145,320 total

includes taxes & fees

Sep 13 - Sep 14

A hot tub with a view of a forested landscape.

9. Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort

Lauren M.

￥110,729 total

includes taxes & fees

Sep 28 - Sep 29

A golf course with a mountain backdrop and autumn foliage.

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

Wintergreen Resort

Justin L.

￥98,591 total

includes taxes & fees

Sep 15 - Sep 16

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

Laurel Ridge

Mindy M.

￥149,127 total

includes taxes & fees

Sep 13 - Sep 14

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

12. Sauna & Hot Tub - 7th Hole Chalet - 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.

￥117,776 total

includes taxes & fees

Sep 23 - Sep 24

A hot tub on a wooden deck with a view of trees.

13. Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort

Christina R.

￥173,998 total

includes taxes & fees

Sep 30 - Oct 1

A spacious kitchen with wooden beams, a central island with stools, and large windows offering a view of the outdoors.

14. Red White & WTG: Hot Tub, 5 Bedrooms!

Pedlars Edge

Kate T.

￥143,424 total

includes taxes & fees

Sep 13 - Sep 14

A wooden staircase with a floral wallpaper background.

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

Laurel Ridge

￥105,717 total

includes taxes & fees

Sep 16 - Sep 17

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

16. Red White and Wintergreen

Pedlars Edge

￥125,518 total

includes taxes & fees

Sep 13 - Sep 14

17. Art & Soul

Nellysford

￥120,525 total

includes taxes & fees

Sep 13 - Sep 14

A wooden deck with a yellow door, a table with chairs, and a rocking chair.

18. Tucked Inn: Upper Unit

Nellysford

￥43,907 total

includes taxes & fees

Sep 13 - Sep 14

A wooden interior with a dining area, a bar, and a seating area.

19. Blue's Barn: Central to Wineries & Breweries

Nellysford

Sarah N.

￥47,350 total

includes taxes & fees

Sep 13 - Sep 14

A house with a porch, a staircase, and string lights.

20. Oasis on 151 • 6BR • Arcade & Pool Table • Hot Tub

Faber

Jennica E.

￥95,933 total

includes taxes & fees

Sep 14 - Sep 15

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Top Wintergreen Hotel Reviews

Newly Built Designer Home in Wintergreen

10/10 Excellent

"Modern interior with all the extras. Beds were comfortable and linens were nice. Kitchen is well appointed. Lots of appropriate storage. We will return next summet"

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

10/10 Excellent

"Just wrapped up a fantastic 3-night stay with my husband and our dog—this place is a total gem! Spacious, spotless, comfy, and truly pet-welcoming with everything you would need including thoughtful touches for the fur baby. We loved the king bed (so comfy!), and cozy fireplace for our surprisingly chilly August nights. You can tell the owner really cares for this place, and it shows in every detail—from the decor, entertainment options, furnishings and more, to the well-stocked kitchen. Also, the location within Wintergreen Resort is ideal. Heather, our host, was super responsive and a real pleasure to rent from. You'd be hard-pressed to find a better place or host."

Family Retreat - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"Great house in a great location. Wonderful getaway for our three generation family vacation (ages 13-85 plus a dog). We really loved the deck, fire pit and hot tub plus the nearby nature trail loop. Cooking for our crowd was easy, and there were multiple places for different groups to hang out. The weather was too wet to do as much outdoors as we wanted but there were lots of things to keep us busy in the house (puzzles, movies, baking, hot tub, games). Highly recommend this great house in Wintergreen Resort."

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews	243
Accommodation	210 Vacation Homes
Lowest Price	￥43,907
Highest Price	￥173,998

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wintergreen vacation homes

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

2. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

3. The Distinguished Squirrel Chalet walking distance

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