Wintergreen, VA Vacation Homes from AED 1,052

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

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

Wintergreen Resort

Stephen M.

AED 1,399 total

includes taxes & fees

27 Aug - 28 Aug

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

Wintergreen Resort

Stanley W.

AED 1,689 total

includes taxes & fees

24 Sep - 25 Sep

3. Mountain Mindset

Laurel Ridge

AED 1,996 total

includes taxes & fees

27 Aug - 28 Aug

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

Nellysford

Robert H.

5. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

AED 1,529 total

includes taxes & fees

27 Aug - 28 Aug

Smart TV, fireplace, table tennis, books

6. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

AED 2,180 total

includes taxes & fees

27 Aug - 28 Aug

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

Chestnut Springs

Cheryl P.

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

Nellysford

Rachel F.

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

Laurel Ridge

Mindy M.

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

Wintergreen Resort

Justin L.

AED 2,863 total

includes taxes & fees

24 Sep - 25 Sep

11. 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.

AED 2,846 total

includes taxes & fees

2 Sep - 3 Sep

12. Pet-Friendly Mountain Retreat with Fireplace & Walkable Village Access Near Wintergreen Resort, Virginia

Wintergreen Resort

AED 1,085 total

includes taxes & fees

10 Sep - 11 Sep

House, Private Bathroom (Red White Wintergreen) | Exterior

13. Red White and Wintergreen

Pedlars Edge

AED 3,007 total

includes taxes & fees

27 Aug - 28 Aug

Coffee/tea maker, fridge, microwave, oven

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

Laurel Ridge

5 bedrooms, desk, iron/ironing board, WiFi (free)

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

Pedlars Edge

Kate T.

AED 3,436 total

includes taxes & fees

27 Aug - 28 Aug

House, Private Bathroom (Art & Soul) | Exterior

16. Art & Soul

Nellysford

AED 2,887 total

includes taxes & fees

27 Aug - 28 Aug

House, Private Bathroom (Tucked Inn: Upper Unit) | Terrace/patio

17. Tucked Inn: Upper Unit

Nellysford

AED 1,052 total

includes taxes & fees

30 Aug - 31 Aug

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

Nellysford

Sarah N.

19. Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton

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

Faber

Jennica E.

AED 2,304 total

includes taxes & fees

31 Aug - 1 Sep

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Top Wintergreen Hotel Reviews

Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

10/10 Excellent

"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

10/10 Excellent

"Overall it was a quiet wintergreen summer experience. Close to the market and inn though we didn’t use either on the trip. Kitchen had the basics but don’t plan to prep anything complicated."

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

10/10 Excellent

"We had a great stay! This place has all we could need. We were able to cook what we wanted with ease. We appreciated having a real coffee maker and not just a Keurig. Loved that it was pet friendly. I had a question for the owner and received a very quick response which was greatly appreciated. Overall, would recommend!"

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

10/10 Excellent

"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"House was great for our family vacation. An actual million dollar view. Family had a wonderful week enjoying the surrounding area with hiking, fishing and local distilleries.House is very well appointed and our host Aubrey was excellent with communication before and during our trip. One tip- Definitely suggest bringing as much food supply as possible to save some driving time to store."

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