Monthly Rentals in Windsor

We really loved our stay at Carrie's place in Pittsfield. She was a fantastic host: responsive, friendly, and proactive. The apartment is so cozy and well-equipped, and we felt at home right away. My dog absolutely LOVES the backyard, and has spent all winter doing snow zoomies every chance he gets. The area is peaceful, but being close to neighbors makes us feel like we're not isolated. All the everyday necessities we need (groceries, doctors, vets, car repair) are a 3-5 minute drive away, and downtown have a ton of cute shops and cafes. There's also a bunch of great sledding and skiing options nearby, and if we come back in the summer, we're going to be sure to check out the nearby trails. We truly enjoyed our time here and would come back in a heartbeat! Thank you Carrie!

Five couples enjoyed two nights at Elizabeth's lovely home. It was the perfect size home for the 10 of us. The kitchen has everything you need. The home was very clean. Elizabeth is very responsive and was able to get us in an hour early. Be sure to read the history of the home which can be found in the library. We were able to enjoy happy hour on the deck with the late afternoon sun shining on us. The home is on a very quiet and peaceful road. We highly recommend this home! Dalton HD Pizza has great pizza. We hiked at The Boulders in Dalton and the Mass Audubon's Pleasant Valley Wildlife Sanctuary in Lenox . We also really enjoyed the Norman Rockwell Museum in Lenox.

All we could say when we reached the property was, “wow”! The stone on the cabin, the colorful foliage that surrounded the property, and the privacy made for a perfect getaway. Close to the city of Adams and Mt. Greylock made for a beautiful experience of the picturesque and awe inducing mountain ranges.

A group of friends and I rented this space for our trip to Berkshire East. This was the perfect space that was a fair distance from the mountain. I really recommend this spot for anything! Ski trips, getaways, etc. We had a blast and Karen was a great host. We will definitely be back!