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

Art & Soul

Nellysford

HK$6,162 total

includes taxes & fees

28 Jul - 29 Jul

Beautiful 4-season Mountain Home- New Listing

Wintergreen Resort

Chad H.

HK$4,243 total

includes taxes & fees

14 Jul - 15 Jul

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

Chestnut Springs

Cheryl P.

HK$4,288 total

includes taxes & fees

14 Jul - 15 Jul

4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs

Laura J.

HK$4,635 total

includes taxes & fees

14 Jul - 15 Jul

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort

Stephen M.

HK$3,235 total

includes taxes & fees

16 Jul - 17 Jul

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

Wintergreen Resort

Stanley W.

HK$2,904 total

includes taxes & fees

9 Aug - 10 Aug

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

Nellysford

Rachel F.

HK$6,858 total

includes taxes & fees

15 Jul - 16 Jul

The Distinguished Squirrel Chalet walking distance

Treeloft

Mark H.

HK$3,410 total

includes taxes & fees

20 Jul - 21 Jul

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

Laurel Ridge

Mindy M.

HK$7,813 total

includes taxes & fees

27 Jul - 28 Jul

Relaxing Wintergreen Chalet

Chestnut Springs

richard r.

HK$3,486 total

includes taxes & fees

9 Aug - 10 Aug

Mountain Mindset

Laurel Ridge

HK$3,741 total

includes taxes & fees

14 Jul - 15 Jul

Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort

Christina R.

HK$8,349 total

includes taxes & fees

15 Jul - 16 Jul

Serene Wintergreen Retreat, Nestled in the Trees

Wintergreen Resort

"We had a wonderful stay. The house was great. The big windows allowed you to view nature up close and personal. The pizza oven was amazing and so was the hot tub. The only problem was the driveway. We knew it was steep but apparently because of winter snow and ice, the asphalt was washed away and it was difficult to navigate without scraping the bottom of car. I would still rate it 10 because it was wonderful. "

Sherryl S.

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.

HK$6,327 total

includes taxes & fees

19 Jul - 20 Jul

Upscale and Family-Friendly in Wintergreen

Roseland

Hunter C.

Mountain Retreat: Year-Round Getaway, Pup Friendly

Laurel Ridge

HK$4,252 total

includes taxes & fees

14 Jul - 15 Jul

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

Nellysford

Hot Tub | Fire Pit | River | State Park | King Bed

Wingina

Melissa C.

HK$2,241 total

includes taxes & fees

20 Jul - 21 Jul

Forever Farm

Schuyler

Hillside Haven: Modern Retreat, Mountain Views

Faber

Shiloh F.

HK$3,037 total

includes taxes & fees

15 Jul - 16 Jul

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Top Wintergreen Hotel Reviews

Where the Trail Ends

10/10 Excellent

"My husband and I came for our anniversary. The place was perfect for the two of us. Enjoyed coffee each morning in the little deck. Very clean and we could walk to the Market and dinner. Keith communicated with us each day."

Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!

10/10 Excellent

"Wonderful condo, exactly as described with everything you could need for a mountain getaway. We stay at Wintergreen a few times a year and this was far and away our favorite place to stay. The host was also wondering and responsive when I had a few questions. Can't wait to stay again in the future."

Lofty Pursuits: Spectacular View + EV Charger

10/10 Excellent

"I loved staying in a treehouse with a great mountain view. The property is beautiful, and the view is spectacular. The hosts have every detail in place--I appreciate that the property and business are woman-owned. We are definitely coming back!!"

Luxury Condo in the Sky! Finest in Wintergreen!

10/10 Excellent

"This listing was exactly as described: it is very accommodating, VERY clean, and the views are spectacular!!!! Our host was clear with check in and check out processes and quick with all responses. It would have been nice to have been informed that every activity and food option close to the condo was closed by 6pm (especially since traveling with teenagers) and everything is at least a 30 minute drive away off of the resort. It also would have been helpful to have information on what was accessible at the resort on location and what was not. Despite those little inconveniences, we thoroughly enjoyed our stay!"

Endless Mountain Top Views from All The Way Up!

10/10 Excellent

"We had a wonderful stay at All the way Up! All of the amenities you could need and more! Hair dryer with diffuser and blow out attachments, no need to bring your own. Pack n Play was clutch. Our 4 month old even took a 1.5 hour nap without having to be held so we could utilize the Couples Connect game. Well stocked kitchen, bathrooms, laundry room. Tyler and Mary were very accommodating when we were worried about unpacking in the storm and were very responsive throughout the stay. We'd definitely stay again. Unmatched views of the blue ridge!"

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