Wintergreen, VA Vacation Homes from AED 1,332

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Our top choices for Wintergreen vacation homes

A cabin with a large window, surrounded by trees.

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

Wintergreen Resort

Stanley W.

AED 1,332 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Nellysford

Dean G.

AED 1,716 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Wintergreen Resort

Maija

AED 1,672 total

includes taxes & fees

25 Oct - 26 Oct

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 bedroom with a wooden headboard, a bed with a plaid blanket, a nightstand with a lamp, a dresser, and a window with a view of trees.

5. Walk to SKi Slopes and Hot Tub

Treeloft

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

6. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

AED 2,175 total

includes taxes & fees

1 Nov - 2 Nov

A deck with outdoor furniture, a table, and a view of the surrounding nature.

7. Merryland with Wintergreen Advantage

Wintergreen

An attic room with a pool table, gaming console, and seating area.

8. Blackrock Canopy

Nellysford

AED 2,821 total

includes taxes & fees

4 Nov - 5 Nov

A cozy living room with a fireplace, comfortable seating, and a large window overlooking a forest.

9. Wintergreen Resort, Hot Tub, Trails, and Ski!

Nellysford

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

10. 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.

A golf course with a mountain backdrop and autumn foliage.

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

Wintergreen Resort

Justin L.

AED 2,252 total

includes taxes & fees

3 Nov - 4 Nov

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

12. Adventure Awaits

Laurel Ridge

Kaden C.

AED 2,194 total

includes taxes & fees

4 Nov - 5 Nov

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.

AED 2,042 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Chestnut Springs

Cheryl P.

AED 2,319 total

includes taxes & fees

25 Oct - 26 Oct

A hot tub with a view of a forested landscape.

15. Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort

Lauren M.

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

Wintergreen Resort

A rustic cabin surrounded by a forest with a stone wall and a wooden deck.

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

Roseland

Allen M.

AED 3,221 total

includes taxes & fees

25 Oct - 26 Oct

A wooden deck with outdoor seating and a fire pit.

18. Mountain Mindset

Laurel Ridge

AED 2,353 total

includes taxes & fees

16 Nov - 17 Nov

A room with a massage chair, exercise bike, and a treadmill.

19. The Black Walnut - Your Own Private Resort

Nellysford

A hot tub area with wooden deck, wicker chairs, and a glass door leading to a sauna.

20. Upscale and Family-Friendly in Wintergreen

Roseland

Brian Z.

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Top Wintergreen Hotel Reviews

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!"

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent

"We were so fortunate to find this spectacular gem! The breathtaking views that pictures just cannot do justice for were amazing! The unit was so well stocked with all the essentials and one of the cleanest places we have stayed. Check-in and check-out were clear and simple. We can’t wait to book again. Thank you for sharing your piece of mountain with us. We loved it."

Family Retreat - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"The house was perfect. Kevin and Jen were VERY responsive to questions. I was unable to take the trash down to the dumpster and Kevin was super accommodating and offered a quick solution. We would absolutely stay there again. Highly recommended."

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

10/10 Excellent

"Great unit. Clean and well supplied with everything you need if you plan to prepare meals. Communication with host (Rebecca) was excellent. If you are planning to eat out and don't want to drive a long distance down the mountain and outside the Wintergreen resort, options are limited. On the resort there are 2 pizza places (which we did not try), plus The Edge (we ate there twice and it was fine), plus Devil's Knob Grill (appears to be the nicest place) but it has a restrictive member/guest policy and staying in a VRBO does not qualify."

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

10/10 Excellent

"What a lovely slopeside condo! Our family had a wonderful stay. The double bunk beds were perfect for our kids. And we loved watching the beautiful sunrise over the mountains. Everything was very clean and comfortable. Thank you for hosting us!"

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

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