Search Vacation Homes in Pittsfield

"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."

"Wonderful view, peaceful quiet area, cosy cabin."

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

"Great spot on the lake. Super quiet and relaxing."

"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "

"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"