Wintergreen, VA Vacation Homes from AED 1,052

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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

31 Aug - 1 Sep

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

31 Aug - 1 Sep

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

Nellysford

Robert H.

AED 1,977 total

includes taxes & fees

30 Sep - 1 Oct

Smart TV, fireplace, table tennis, books

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

Chestnut Springs

RK D.

AED 2,180 total

includes taxes & fees

31 Aug - 1 Sep

5. Mountain Mindset

Laurel Ridge

AED 1,893 total

includes taxes & fees

31 Aug - 1 Sep

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

Chestnut Springs

Cheryl P.

7. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

AED 1,958 total

includes taxes & fees

16 Sep - 17 Sep

8. 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

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

Nellysford

Rachel F.

AED 3,205 total

includes taxes & fees

8 Sep - 9 Sep

10. Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort

Lauren M.

AED 2,626 total

includes taxes & fees

28 Sep - 29 Sep

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

Wintergreen Resort

AED 2,347 total

includes taxes & fees

1 Sep - 2 Sep

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

Laurel Ridge

Mindy M.

AED 3,573 total

includes taxes & fees

31 Aug - 1 Sep

13. 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

14. Red White and Wintergreen

Pedlars Edge

AED 3,007 total

includes taxes & fees

31 Aug - 1 Sep

15. Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Resort

Neda A.

Coffee/tea maker, fridge, microwave, oven

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

Laurel Ridge

AED 2,166 total

includes taxes & fees

31 Aug - 1 Sep

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

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

Pedlars Edge

Kate T.

AED 3,436 total

includes taxes & fees

31 Aug - 1 Sep

House, Private Bathroom (Art & Soul) | Exterior

18. Art & Soul

Nellysford

AED 2,887 total

includes taxes & fees

31 Aug - 1 Sep

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

19. Tucked Inn: Upper Unit

Nellysford

AED 1,052 total

includes taxes & fees

31 Aug - 1 Sep

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Top Wintergreen Hotel Reviews

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!"

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."

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."

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