Wintergreen Vacation Homes

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 holiday homes

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

Wintergreen Resort

Stanley W.

HK$2,740 total

includes taxes & fees

16 Aug - 17 Aug

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

Wintergreen Resort

Stephen M.

3. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

HK$3,102 total

includes taxes & fees

4 Aug - 5 Aug

4. Beautiful 4-season Mountain Home- New Listing

Wintergreen Resort

Chad H.

HK$4,210 total

includes taxes & fees

1 Sept - 2 Sept

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

Chestnut Springs

Laura J.

HK$4,773 total

includes taxes & fees

24 Aug - 25 Aug

6. Relaxing Wintergreen Chalet

Chestnut Springs

richard r.

HK$3,550 total

includes taxes & fees

14 Aug - 15 Aug

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

Chestnut Springs

Cheryl P.

HK$4,290 total

includes taxes & fees

4 Aug - 5 Aug

8. Mountain Mindset

Laurel Ridge

HK$4,491 total

includes taxes & fees

1 Sept - 2 Sept

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

Nellysford

Rachel F.

HK$7,107 total

includes taxes & fees

1 Sept - 2 Sept

10. Adventure Awaits

Laurel Ridge

Kimberly K.

HK$5,376 total

includes taxes & fees

6 Aug - 7 Aug

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.

13. Family-Friendly Meets Luxury

Pedlars Edge

Ary S.

HK$8,684 total

includes taxes & fees

5 Aug - 6 Aug

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

Wintergreen Resort

Justin L.

HK$5,500 total

includes taxes & fees

11 Aug - 12 Aug

15. Luxury Oasis w/outdoor lounge! Hiking, lakes, brew trails & golf. Pet friendly!

Chestnut Springs

Marissa L.

16. Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort

Christina R.

HK$8,353 total

includes taxes & fees

9 Aug - 10 Aug

17. 6BR w/ Pool near Wintergreen & Wineries, Sleeps 19

Nellysford

18. Red White and Wintergreen

Pedlars Edge

HK$5,980 total

includes taxes & fees

4 Aug - 5 Aug

19. Upscale and Family-Friendly in Wintergreen

Roseland

Hunter C.

20. Privacy and Views in Wintergreen

Wintergreen Resort

Anna C.

HK$9,326 total

includes taxes & fees

15 Aug - 16 Aug

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Top Wintergreen Hotel Reviews

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

10/10 Excellent

"Condo was very clean, host was attentive. Location is great. Just a short walk to the market and the Edge. Great for a family of 5!"

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

10/10 Excellent

"Property was clean and comfortable for our summer weekend stay. Host is responsive and anxious to make sure everything is just right. Kitchen and bathroom are well stocked with essential oils, coffee and teas, toiletries,paper and cleaning supplies.The sunset view from the balcony, dining and living room is outstanding.The decor throughout the residence has a professional touch and is charming. Fire and Frost bakery and pizza is a short walk away. Overall, this is a strong choice and a good bet if you are staying at Wintergreen."

Endless Mountain Top Views from All The Way Up!

10/10 Excellent

"This beautiful unit at the top of Wintergreen Resort does not disappoint in any way. The location and views of the beautiful Blue Ridge mountains make you quickly forget the stressors of your at-home life! The furnishings are high-end, kitchen well equipped and bedding comfortable. The communication from the hosts is the best I’ve experienced in 15 years of vacation rental bookings. It is very obvious that the quality of our stay was their highest priority. Highest recommendation."

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"The house was very nice. The view for the one day we had it (darn Canadian fires) was amazing and the fire pit at the lower level was enjoyed. The beds and linens were very comfortable. The kitchen was well equipped. The only negative was it was warm in the house and the hot tub wasn’t the cleanest."

Find out more about Wintergreen