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2 Jum. I - 4 Jum. I

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Compare 444 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

"What a great spot to stay for the few days we were there Can’t wait to come back! "

SAR 859 total

includes taxes & fees

3 May - 4 May

"Very kinda hosts, and wonderful house."

SAR 3,882 total

includes taxes & fees

28 Apr - 29 Apr

"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "

"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."

"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "

"Perfect location for a peaceful, scenic vacation."

"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "

"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "

"Great house that has everything for the family vacation "

"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "

"We spent a wonderful weekend at this truly stunning property! The house is incredible, so well equipped, every detail has been thought of and the interior is beautiful. The outdoor spaces are amazing, the pool, hot tub, fire pit, outdoor seating, beautiful gardens are stunning! The location of the house is perfect, so close to lots of farms and orchards. We so look forward to making a return visit I!"

"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "

"Beautiful property, well-appointed, and comfortable for extended family of 12."

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

"Beautiful house in a quiet location. Perfect for our trip to go see The Norman Rockwell museum , Stockbridge Christmas holiday lights only about 25 minutes away. "

"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."

"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "

"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"

"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "

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Other property types in Pittsfield

"Very kinda hosts, and wonderful house."

SAR 3,882 total

includes taxes & fees

28 Apr - 29 Apr

"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! "