Search Vacation Homes in Windsor

"Very clean and nice apartment in a pleasant little city."

"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...

"We were delighted with our rental house that was tastefully put together, beautiful hardwood floors, 3 bedrooms and baths each on separate floors for more privacy for everyone. It is locate near many hiking trails and close to a quaint town. The country setting and babbling brook passing nearby was an escape from all the noise in our world."

"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."

"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...

"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...

"We liked the fact that it was very quiet, perfectly described, had an amazing view and was beyond peaceful. The gardens and landscape made the setting even better. Wished we were in the area longer so we could’ve stayed longer. Would definitely book this suite again. "

"Worked well for our small team. Close enough to the base area to walk."

"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"

"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"

"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"

"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"

"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."

"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."

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

"My BF and I really enjoyed the Hawley Home. The location was stunning and quiet. The owner was very kind and responsive when I reached out with questions before we started out on our drive to the location. There was a welcome book with all of the information on the home and it included information about the local attractions. The property is clean, the bed is comfortable and the views are breathtaking. There is no cell service ( not that is a bad thing with as much as we work) but the home has...

"The tiny house was absolutely relaxing. It was perfectly located close enough to the main are but yet far enough away for peace. The hosts were so quick to respond and the house was clean and welcoming, hot tub was amazing! Can’t wait to go back!!"

"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"