Wintergreen, VA Vacation Homes from AED 1,318

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.

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

Wintergreen Resort

Stanley W.

AED 1,318 total

includes taxes & fees

7 Sep - 8 Sep

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

Nellysford

Robert H.

AED 1,591 total

includes taxes & fees

8 Sep - 9 Sep

4. Mountain Mindset

Laurel Ridge

AED 2,050 total

includes taxes & fees

9 Sep - 10 Sep

Smart TV, fireplace, table tennis, books

5. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

AED 2,186 total

includes taxes & fees

8 Sep - 9 Sep

6. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

AED 2,138 total

includes taxes & fees

6 Oct - 7 Oct

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

Nellysford

Rachel F.

8. Private Mountain Getaway Wintergreen Resort

Chestnut Springs

AED 2,561 total

includes taxes & fees

7 Sep - 8 Sep

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

Wintergreen Resort

Justin L.

AED 2,741 total

includes taxes & fees

18 Sep - 19 Sep

10. Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort

Lauren M.

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

Laurel Ridge

Mindy M.

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.

AED 2,846 total

includes taxes & fees

13 Sep - 14 Sep

House, Private Bathroom (Red White Wintergreen) | Exterior

13. Red White and Wintergreen

Pedlars Edge

AED 3,007 total

includes taxes & fees

7 Sep - 8 Sep

14. Wintergreen 5BR with Hot Tub, Sauna, Firepit

Chestnut Springs

David S.

15. Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort

Christina R.

AED 4,158 total

includes taxes & fees

30 Sep - 1 Oct

16. Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Resort

Neda A.

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

Laurel Ridge

AED 3,865 total

includes taxes & fees

18 Sep - 19 Sep

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

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

Pedlars Edge

Kate T.

AED 3,436 total

includes taxes & fees

7 Sep - 8 Sep

House, Private Bathroom (Art & Soul) | Exterior

19. Art & Soul

Nellysford

AED 2,887 total

includes taxes & fees

20 Sep - 21 Sep

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Top Wintergreen Hotel Reviews

Wintergreen cabin, hot tub, sauna, walk to trails

10/10 Excellent

"Property was in good condition and stocked with everything we needed. Checkin was super simple and host was very responsive. Will visit again."

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."

Newly Built Designer Home in Wintergreen

10/10 Excellent

"This is one of the finest properties we've ever visited in all of our trips to Wintergreen. We have been coming since 1978. The location is great. It's snuggled into the lower elevations of the resort. That will pay dividends during your stay. Less vehicular and foot traffic. Combine that with easy access to the Appalachian Trail for some of the best hiking and views in the Blue Ridge. Ideal for kids and pets.The property itself? Beautiful, clean, tasteful, accommodating. The lighting and furnishings are designer quality. The well stocked kitchen is a joy to use with all of the necessary gadgets and utensils. Prefer pour over coffee? Your goose neck kettle is waiting. More of a French press kind of person? The Fellow Clara press is ready to go.The bedrooms and bathrooms are beautifully appointed. The wifi and entertainment setup are top drawer. You will not be disappointed. Highly recommended!"

Updated! Sleeps 14 - 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."

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

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