Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

Our top choices for Winchester holiday homes

"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "

includes taxes & fees

25 Sept - 26 Sept

"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."

"The spot was amazing and everything was exactly what we wanted. "

Smart TV, fireplace, DVD player, ping pong

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"

"Nice house in a nice location. "

includes taxes & fees

25 Sept - 26 Sept

"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...

"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."

"Quite secluded clean comfy cabin We enjoyed it very much. Very close to the things we wanted to do."

3 bedrooms, travel cot, free WiFi, bed sheets

"We really appreciated the solitude and quiet retreat this cabin offered. "

"Great place and convenient to get to and from Berkshire East."

"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"

"Very clean, well equipped and thoughtfuly supplied. An extra bonus were the great assortment of books, games, movies, and puzzles available. A great deal of experience and generosity went into choices made, and it was much appreciated. "

"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"

"Nice and comfy - loved the decor and the property."

"There was a bit of a mix up during the check in process, but it was straightened out. Luckily for us this was trip to catch up with family and friends so we could go somewhere to figure it out, as there is no service without the wifi. The house is gorgeous, clean and spacious inside. There is some sort of day camp (?) thing going on at the property next to it, so kids are running around and swimming in that area all day. It wasn’t bothersome to us. Also the road getting to the place is full of...

"The location was perfect, no traffic and nice walking area. The house has such a wonderful lay out with 2 living/sitting rooms so all family members could enjoy their own space then enjoy nice family meals on the big dining table together."