Search Vacation Homes in Windsor

"Easy check in and the owner responds immediately to any questions. A really easy close drive to Berkshire East Ski Mountain. "

"Stayed here multiple times and will come back again. Great place to stay…"

"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."

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

"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."

"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "

"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...

"Very quaint location, clean property, and great place to stay"

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"A cozy spot to watch the snow come down!"