Search Vacation Homes in Pittsfield

"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...

"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"

"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...

"Beautiful property- well maintained and excellent location."

"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!"

"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."

"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"

"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 cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."

"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...

"This was a great house! They thought of all the details, had everything you could need. Hot tub was clean and entire house was spotless. Beds were comfortable. Great location, so close to downtown Great Barrington, cute shops and restaurants. And also super close to lots of hikes and ski mountain etc. We had a really fantastic stay and would stay again and recommend!"

"We had such a nice weekend at this beautiful home! The location was great, there were awesome views, and Marc was a very kind, courteous host! He was very easy to get ahold of if we had any questions. The hot tub was very relaxing and spacious. Also, it had all of the necessities. If you are looking for a family-friendly winter rental this is a great place to book."

"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...