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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Wintergreen vacation homes

1. 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

12 Aug - 13 Aug

2. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

AED 1,486 total

includes taxes & fees

12 Aug - 13 Aug

Smart TV, fireplace, table tennis, books

3. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

Laura J.

AED 2,281 total

includes taxes & fees

26 Aug - 27 Aug

4. Mountain Mindset

Laurel Ridge

AED 2,108 total

includes taxes & fees

31 Aug - 1 Sep

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

Wintergreen Resort

Stephen M.

AED 1,950 total

includes taxes & fees

15 Aug - 16 Aug

6. Beautiful 4-season Mountain Home- New Listing

Wintergreen Resort

Chad H.

AED 2,001 total

includes taxes & fees

12 Aug - 13 Aug

7. Relaxing Wintergreen Chalet

Chestnut Springs

richard r.

AED 1,547 total

includes taxes & fees

13 Aug - 14 Aug

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

Chestnut Springs

Cheryl P.

9. Adventure Awaits

Laurel Ridge

Kimberly K.

AED 2,402 total

includes taxes & fees

22 Aug - 23 Aug

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

Nellysford

Rachel F.

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

Laurel Ridge

Mindy M.

AED 3,661 total

includes taxes & fees

24 Aug - 25 Aug

Coffee/tea maker, fridge, microwave, oven

12. Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10

Pedlars Edge

Hesham A.

AED 2,780 total

includes taxes & fees

10 Sep - 11 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 2,778 total

includes taxes & fees

19 Aug - 20 Aug

House, Private Bathroom (Red White Wintergreen) | Exterior

14. Red White and Wintergreen

Pedlars Edge

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

Wintergreen Resort

Justin L.

AED 2,762 total

includes taxes & fees

10 Sep - 11 Sep

16. Privacy and Views in Wintergreen

Wintergreen Resort

Anna C.

3 bedrooms, iron/ironing board, WiFi (free), bed sheets

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

Laurel Ridge

AED 2,669 total

includes taxes & fees

10 Sep - 11 Sep

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

Pedlars Edge

Kate T.

AED 3,589 total

includes taxes & fees

12 Aug - 13 Aug

House, Private Bathroom (Art & Soul) | Exterior

19. Art & Soul

Nellysford

AED 2,887 total

includes taxes & fees

12 Aug - 13 Aug

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

20. Tucked Inn: Upper Unit

Nellysford

AED 1,052 total

includes taxes & fees

12 Aug - 13 Aug

View all properties

Find vacation rentals that suit your style

Cabins

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Wintergreen Hotel Reviews

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

10/10 Excellent

"Our stay at the property was amazing! Everything in the description was absolutely on point except for the views. They were so much better, but thats to be expected as those views are hard to describe! My family spent most of the time on the porch! The hosts were very helpful and very quick to respond! Overall a 5 star stay! We definitely recommed this condo and hope to come back here on our next vivst!"

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

10/10 Excellent

"Beautiful condo close to the Mountain Inn. Kitchen is well stocked and the owners provide a lot for your furry companions. We had a great time hiking the trails and coming back for a quiet evening. Wonderful place to stay and I can't wait to come back!!"

Cozy Cabin with private HOT TUB!

10/10 Excellent

"We had a great time this weekend in your cozy cabin. There was just enough room for everyone and we were all quite comfortable. The nature around the cabin was so pretty, and we had tons of beautiful butterflies visit us. We ended our afternoons with a nice dip in the hot tub, which is a nice addition to the home. The hosts were very accommodating when we needed local information as well. Thank you so much for allowing us to stay in your home."

New Build! Log Cabin with Hot Tub in Wintergreen

10/10 Excellent

"We absolutely loved our stay at this beautiful cabin-style home in the woods! It was the perfect setting for our reading retreat and gave us plenty of space to relax, unwind, and spend time together.The living room was so cozy and perfect for curling up on the couch with a good book. The kitchen was fantastic and had everything we needed to make meals during our stay. We especially loved the large farmhouse-style table - it was perfect for puzzles, games, and gathering together.The beds were comfortable and the rooms were bigger than expected. The home was beautiful and welcoming, and the entire space was thoughtfully laid out for a relaxing getaway. We truly enjoyed our stay and would absolutely love to come back!"

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"My family had a wonderful time here. The view is stunning and absolutely never got old. We had 6 adults and 2 kids and plenty of space. The pool table and arcade games kept the kids busy even on raining days and they loved scrambling on the rocks by the eagles nest. The adults loved the sauna and steam showers. The location is convenient to many awesome hikes and there’s some great restaurants and breweries in the area but be prepared to drive a bit for fresh produce. The family is already talking about going back. Definitely recommend this place."

Endless Mountain Top Views from All The Way Up!

10/10 Excellent

"Great location with amazing views, perfect size living space, and everything we needed. Easy access to walking, hicking, swimming, golf, spa, food, etc. Short drive to wineries, recreational lake and local restaurants. Really didn't have to leave the mountain for much. Super enjoyable vacation!!!"

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wintergreen vacation homes

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

2. The Distinguished Squirrel Chalet walking distance