Wintergreen, VA Vacation Homes from AED 1,722

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

A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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

Wintergreen Resort

Maija

A cabin with a large window, surrounded by trees.

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

Wintergreen Resort

Stanley W.

A modern kitchen with wooden beams, a large island, and a dining area with a bench.

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

Nellysford

Dean G.

AED 1,722 total

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

4. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

A cabin with a deck, outdoor seating, and a fire pit.

5. Walk to SKi Slopes and Hot Tub

Treeloft

A two-story cabin with a balcony, surrounded by trees.

6. Blackrock Canopy

Nellysford

AED 2,780 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a stone fireplace, a large window with a view of trees, a ceiling fan, and a yellow sofa.

7. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

AED 2,024 total

includes taxes & fees

2 Nov - 3 Nov

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

Chestnut Springs

Cheryl P.

A balcony with wicker furniture and a table, overlooking a scenic view of mountains and autumn foliage.

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

Nellysford

Rachel F.

A covered outdoor seating area with a grill and fire pit, surrounded by cushioned chairs, overlooking a forested area.

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

Wintergreen Resort

Justin L.

A two-story cabin with a deck, large windows, and a hot tub.

11. Fall Getaway | Sauna & Hot Tub | 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 2,808 total

includes taxes & fees

2 Nov - 3 Nov

12. Blackrock Canopy: Walk to Ski + 2 Living Spaces

Wintergreen Resort

A deck with a fire pit, outdoor furniture, and a view of trees and a sunset.

13. Wintergreen cabin, 5 min to ski, hot tub, sauna

Chestnut Springs

mikenzi b.

A stone fireplace with a fire, a leather armchair, a patterned armchair, and a tray with candles.

14. Blue Ridge Mt retreat steps off the Appalachian Trail in Wintergreen Resort

Roseland

Allen M.

AED 3,062 total

includes taxes & fees

2 Nov - 3 Nov

A cozy outdoor seating area with a fire pit, wooden deck, and a large wooden barrel.

15. Family-Friendly Meets Luxury

Pedlars Edge

Ary S.

A wooden deck with outdoor seating and a fire pit.

16. Mountain Mindset

Laurel Ridge

AED 2,045 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with large windows, a wooden ceiling, and a chandelier.

17. Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Resort

Helen B.

A covered porch with two chairs and a table, surrounded by a wooden railing, overlooking a forested area.

18. Adventure Awaits

Laurel Ridge

Kaden C.

A wooden deck with outdoor seating, a railing, and string lights.

19. Privacy and Views in Wintergreen

Wintergreen Resort

Anna C.

A two-story house with a deck, hot tub, and outdoor seating area.

20. Wintergreen Luxury, Breathtaking Views

Wintergreen Resort

Donna C.

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Top Wintergreen Hotel Reviews

Best views on Mountain! Breathtaking 5 Star condo! Available Nov 20-22 weekend!

10/10 Excellent

"What an incredibly special place. Those views are simply mesmerizing, the condo is incredibly well furnished… Completely luxurious. A well stocked kitchen, lots of thoughtful extras. It was truly one of the best rentals we’ve ever stayed in. From start to finish a perfect experience!"

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

10/10 Excellent

"Brilliantly decorated and had the feel of a European apartment. From the moment we walked in, we were blown away by the attention to detail, thoughtful design, and cozy, historic charm. The decor effortlessly blended classic elegance with modern comfort, making it feel like a curated retreat rather than just a rental. Well done, Amy!"

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

10/10 Excellent

"We had a lovely experience staying at this property. We stayed two nights with our 3 kids (ages 5, 7, 9) and we all thoroughly enjoyed the hot tub, Pac Mac console and enjoyed making a fire and roasting s'mores. The house was very clean, beds were comfortable and communication was prompt. We did the Shamokin Falls and Plunge hikes which were very convenient for our young kids. The space was perfect for our needs (we were close to the resort but still felt like we got away and had privacy) - thank you!"

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

10/10 Excellent

"This home was the perfect place for our group of 6 (3 couples)! We were in town for our annual visit to the 151 Brew Trail, and it happened to be Oktoberfest as well! The home is extremely clean, looks identical to the pictures, and is secluded enough without neighbors right in your yard. The observation deck is an added plus. Communication was very fast and reliable, and the check-in and check-out processes were very smooth! We will be staying here from now on for our yearly trip!"

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!

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