Holiday Homes in Wintergreen

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Featured Holiday Homes in Wintergreen

Enjoy cooking in this well-equipped kitchen with a stainless steel range hood, granite countertops, and dishwasher.

"The house was lovely. The location was great. Plenty of space for everyone. We really enjoyed this home."

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. "

includes taxes & fees

19 July - 20 July

Escape to a secluded cabin nestled among the trees, with a cozy porch and deck area.

"Exactly as advertised. Clean, everything worked, great location."

includes taxes & fees

30 July - 31 July

Enjoy al fresco dining on this deck surrounded by lush trees.

"Excellent house close to the slopes"

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."

includes taxes & fees

16 July - 17 July

Escape to a serene natural haven surrounded by lush greenery and a tranquil garden.

"Very cute, clean, and a good location. Everything was in working order and the owners had an up to date resource book that was very handy. Since I love trains, the one that rolled by in the early hours of the morning was a welcome sound."

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!"

Stunning two-story home with a charming front porch and beautifully manicured lawns.

"Had a great time at this great property, will definitely be back!"

Relax in this stylish living room with a grey sofa, console table, and flat-screen TV.

"Great for a quick weekend trip. Centrally located to everything in the valley and just a short trip to UVA Campus."

includes taxes & fees

30 July - 31 July

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 "

Enjoy cooking in this well-equipped kitchen with a microwave, black stove, and stainless steel refrigerator.

"Very nice, clean and quiet!"

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

"Enjoyed our stay. The sunrises and sunsets were great. House was fun. Don’t miss visiting the dairy farm across the street. Lovely. Perfect place for a relaxing time. "

Relax in a serene outdoor setting with a fire pit table and two comfortable chairs.

"Great location, amenities and owner's willingness to address all our questions/issues."

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. "

Stunning golf course views surround this serene residential area with beautifully manicured greens.

"Enjoyed our 2nd year here. Lots of room and fabulous kitchen. "

Enjoy a casual meal in our outdoor dining area, complete with a table set for two and Adirondack chairs for relaxation.

"We loved staying here! The owners were quick to communicate and we had a very simple check-in. The location was beautiful. We enjoyed all the local wineries and distilleries we could possibly fit in and then lit a fire to relax. We had a party of 8 and we fit in perfectly. The home is so cozy and beautifully decorated. 5 stars!. "