Cottages in Wintergreen

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Populaire Cottages in Wintergreen

'We enjoyed this place immensely. Location was convenient to all wineries, great dining, horseback riding, and hiking. We will be back.'

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20 aug - 21 aug

'Beautiful property located on the Piney River. Home has all the conveniences needed to make your stay enjoyable. This was our second stay here and we plan to return again in the future. Only recommendation would be to update the pots and pans provided in the cabin. They have been well used. Do not change anything else!!'

'Tranquil Mountain Getaway. This cottage is amazing and the hosts are always wonderful. Everything is always clean and very welcoming. The river and mountain views make this an excellent location to relax and connect with nature. '

'The guest cottage was perfect for us. Well appointed and exceptionally clean and comfortable with big windows. The deck attached to the main house offers a peaceful view of the hillside. Very happy to have stayed here. Thanks! '

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16 sep - 17 sep

'We had such a great girls weekend!! The Cottage was so cute, fun, clean and beds were super comfy. The house was in the perfect location for everything. Can’t wait to go back. '

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3 sep - 4 sep

'Went for a girls' trip and had a great time. The pool was nice after a long day of exploring the area. '

'Loved staying at the Birds and Bees Cottage. It was so peaceful waking up each day, sitting on the porch and enjoying the views of the farm. This cottage was the perfect spot to unwind after visiting some local wineries. It was quiet and very easy to relax on the porch with a good book in the evening. Hope to return in the fall. '

'The cottage was well equipped and very clean. We loved our stay and so did our two dogs. '

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15 sep - 16 sep

'As pictured. Very clean with modern accommodations!'

'This was perfect for our weekend trip to the 151 breweries/wineries. Very cute house and very clean. We would come back!'

'The home was lovely and I have never seen a VRBO so well stocked with anything you might need. Everything was provided. The creek is a soothing sound and the dogs just loved the yard! Close to some great trails. Very gracious hosts.'

'Clean, well organized, easy to walk and restaurants'

'The Plainfield Cottage is a perfect getaway. We came in for a graduation and were quite busy. However, each time I stepped into the cottage, it felt peaceful, bright and clean. A great retreat to unwind and relax at. Cathy was very attentive on any needs we needed, as there were few because it was well stocked.'

'Very tranquil place. '

'We stayed at this property for the 2025 Washington and Lee graduation. It was the perfect choice because it provided a place to relax with grandparents and our family. The property and house was magnificent with great views of the mountains. The house was spacious and just made you feel at home. The hosts were responsive but not intrusive. Our only regret is that we did not find this property sooner in our 4 years worth of travel back and forth to Lexington. '

'We had a great time!! The house was spotless, hot tub was great, and the fire pit was perfect! We had fun playing pool every night and seeing the animals next door during the day. Master bedroom and bathroom are amazing!!!'

'Great place to stay out in the countryside. All the details taken care of. '

'This was a family gathering to celebrate a UVA graduation. We wanted to stay away from the craziness of Charlottesville. This house was perfect! Everyone in our party raved about how cute, comfy, well laid a house it is! Very well stocked - PLENTY of wine glasses! lol We hit 4 wineries and a brewery (2x) during our stay - all with/in a 5 mile radius! We would highly reccomend and would stay again - for longer - in the future! '