Wintergreen Vacation Rentals

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Browse Select Wintergreen Vacation Homes

Relax on the deck with two comfortable rocking chairs, surrounded by a serene landscape.

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

CA $356 total

includes taxes & fees

Aug 12 - Aug 13

Stroll through the beautifully maintained garden, featuring a variety of flowering plants and shrubs, along a shaded path.

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

Relax in the hot tub surrounded by lush greenery and comfortable seating.

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

Access the upper level or storage area via the wooden staircase.

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

CA $157 total

includes taxes & fees

Aug 13 - Aug 14

Enjoy a warm gathering space with a fireplace, flat-screen TV, and access to an outdoor deck.

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

Enjoy a serene rural retreat with a spacious deck, pool, and hot tub overlooking rolling hills.

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

Enjoy meals at the central dining table in this well-lit kitchen.

"Above and beyond on everything highly recommend staying here"

Enjoy cooking in this well-lit kitchen with an oven, gas stove, and large sink.

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

Enjoy expansive views of the surrounding greenery from the large windows in this room, featuring a cozy seating area and a well-equipped kitchen.

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

Relax in a spacious hot tub with four jets for a rejuvenating soak.

"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!"

Compact kitchen with microwave, stove, and countertop, adjacent to a doorway.

"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. "

Enjoy cooking in this well-equipped kitchen with a stainless steel range hood, window view, and convenient dishwashing machine.

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

CA $417 total

includes taxes & fees

Aug 12 - Aug 13

Enjoy al fresco dining with a barbecue grill and seating area overlooking the surrounding landscape.

"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. "

Relax in this spacious living room with a stone fireplace, comfortable sofa, and large windows.

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

Enjoy dining and socializing on the deck, surrounded by lush greenery.

"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...

CA $882 total

includes taxes & fees

Aug 18 - Aug 19