Wintergreen Vacation Homes

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Our top choices for Wintergreen holiday 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 bedroom with a wooden headboard, a bed with striped bedding, two bedside tables with lamps, and a wooden wardrobe.

2. Wintergreen Resort Chalet w/Fireplace + Deck

Deer Springs

A cabin with a large window, surrounded by trees.

3. 3 mins to skiing! Cozy chalet w/ king beds, fireplace, & hot tub. Dog-friendly!

Wintergreen Resort

Stanley W.

HK$3,373 total

includes taxes & fees

9 Dec - 10 Dec

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

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

Nellysford

Dean G.

HK$3,253 total

includes taxes & fees

9 Nov - 10 Nov

A room with a grey sofa, a white pillow, a plant, a small white shelf with candles and books, and a window with a view of trees.

5. Wintergreen Ski-In/Out: Hot Tub, Sauna, Game Room

Wintergreen Resort

HK$4,578 total

includes taxes & fees

9 Nov - 10 Nov

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

6. The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

HK$2,957 total

includes taxes & fees

9 Nov - 10 Nov

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

7. Blackrock Canopy

Nellysford

HK$5,934 total

includes taxes & fees

16 Nov - 17 Nov

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

8. 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.

HK$4,539 total

includes taxes & fees

9 Nov - 10 Nov

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

9. 4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

RK D.

HK$4,293 total

includes taxes & fees

9 Nov - 10 Nov

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

10. Walk to SKi Slopes and Hot Tub

Treeloft

HK$3,859 total

includes taxes & fees

9 Nov - 10 Nov

A deck with outdoor furniture, a fire pit, and a building entrance.

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

Nellysford

HK$4,383 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Wintergreen Resort

Justin L.

HK$4,471 total

includes taxes & fees

17 Nov - 18 Nov

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

Chestnut Springs

Cheryl P.

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

Wintergreen Resort

HK$6,286 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Nellysford

Rachel F.

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

16. Adventure Awaits

Laurel Ridge

Kaden C.

HK$4,180 total

includes taxes & fees

22 Nov - 23 Nov

A wooden deck with outdoor seating and a fire pit.

17. Mountain Mindset

Laurel Ridge

HK$4,386 total

includes taxes & fees

9 Nov - 10 Nov

A residential property with a patio area, outdoor seating, a hot tub, and a fire pit.

18. The Black Walnut - Your Own Private Resort

Nellysford

Chris S.

HK$10,866 total

includes taxes & fees

10 Nov - 11 Nov

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

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

Chestnut Springs

mikenzi b.

HK$3,770 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Roseland

Allen M.

HK$6,536 total

includes taxes & fees

9 Nov - 10 Nov

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Top Wintergreen Hotel Reviews

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

10/10 Excellent

"My wife and I have been going to Wintergreen and/or Massanutten in the fall for more than 20 years, and this was our best experience. This truly is the "best view" on either mountain. We've never rented a better condo or had a more accommodating host. We didn't even use many of the things that we brought with us because the unit was so well stocked. It cost a bit more than some of the other units, but it was well worth it. We will definitely be back."

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

10/10 Excellent

"We had a fantastic short stay here! The condo was just right for our family of four plus pup. Everything was as perfect as it could be. Just as pretty / possibly even more so as the photos. The kitchen and every other part of the condo was well stocked with everything we could possibly need. Lots of fun games, nightlights to help at night, and they even provided a dog blanket. When the Wii remote needed new batteries (hardly an urgent issue!), Heather responded almost instantaneously with info on where to find backups in the condo. We will be back!"

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

10/10 Excellent

"Such a perfect little condo - I loved every bit of it! I traveled solo and felt very safe. It had everything I needed and was within walking distance of a market and the resort. Communication with the host was great and they were very responsive when I needed assistance. I will definitely stay here again!"

Blue Ridge Cabin · Hot Tub· 3 Levels · 3 Scenic Decks · Music Game Room · Arcade

10/10 Excellent

"An excellent house, situated in a charming location that offers great privacy. It is very clean, tidy, and well-maintained. The hosts are extremely responsible and provide excellent service; they are always attentive to their guests' needs."

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

10/10 Excellent

"My wife Teresa and I have been renting this condo for 12 yrs in a row. For the money, its the best rental in Wintergreen! Already booked and paid for for next year's visit. Accessibility is another plus with this condo that no one ever mentions. we are both 60 yrs old so this is important and if you have kids, lugging a bunch of stuff up and down stairs sucks. This is not an issue at this condo. Parking is only feet from the foyer door and then a few steps up and you are at the condo door. Huge value for the money!"

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