You can pick up the new and old Appalachian Trails near Wintergreen. We had a lovely walk even on a cold winter day.

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Vacation Homes in Wintergreen

"This is a very comfortable, wonderfully quiet place. Excellent spot for a family. "

￥37,369 total

includes taxes & fees

Aug 17 - Aug 18

"Thanks for a wonderful stay at your beautiful farm! Great location for visiting wineries and Charlottesville."

"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"

"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."

￥16,905 total

includes taxes & fees

Aug 12 - Aug 13

"Second time staying here and we had the best time. Great for a weekend getaway to hang out with friends and family. "

"We had a great time. Very pretty house in a very pretty setting!"

"Above and beyond on everything highly recommend staying here"

"This was a great place with a great location! 10/10 would stay here again."

Smart TV, fireplace, video games, DVD player

"The house was perfect for us. Plenty of space for everyone to hang out together. "

"Check-in process was a breeze, communication with the hosts was super easy and consistent. Place was very clean and exactly as appears in the pictures. My group had an amazing time and loved the location of this property. Would 110% stay here again!"

"We traveled to VA from NY. Check in was easy and simple. As was checkout. It was conveniently located to a lot of places. Would stay again "

"House was perfect for a weekend of skiing. You’re able to walk to the resort from the house which was a huge plus since it was a packed weekend. Overall great stay! "

"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "

"Beautiful property and very responsive host. Nice place to stay. "

￥44,223 total

includes taxes & fees

Aug 11 - Aug 12

"Loved the home! Was a perfect experience for us."

"Beautiful place! Amazing views! Great hospitality! Has everything you need! Plenty of amenities. Host provided everything we needed. "

Smart TV, fireplace, video games, video library

"Perfect place to relax and enjoy the company of friends and family. "

"There were a few little hiccups, the top bunk bar was not attached (not an issue as it wasn’t fully needed) and the oven was broken but I message the owner and he replied back very quickly. Neither were an issue for us. The house was perfect! Plenty of cooking supplies for our crew of 12. We loved the deck and spent plenty of time out there and there were more than enough towels for everyone. The check out rules were very clear and reasonable. I would say that something should be listed for the...

￥94,222 total

includes taxes & fees

Aug 15 - Aug 16