Search Vacation Homes in Windsor

"We enjoyed our stay at the tiny home!"

"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"

"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "

"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."

"A very good place to stay. Best of all, each bedroom has its own bathroom. There's plenty of hot water, even if multiple people are showering at the same time. The only downside to me is that the washer is broken when we checked in. We want to come again!"

"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "

"The home is very nice and cozy. It really felt like a comfy home."

"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."

"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "

"Exactly what you want in a ski house!"

"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."