Search Vacation Homes in Pittsfield

"The schoolhouse was just what we were looking for- a quiet country location with good walking, hiking, exploring, and close to Randolph. We appreciated the ephemera- books, maps, newspapers. Looking through the shelves and cabinets was an adventure unto itself. We spend time outdoors so one plus would have been more comfortable outdoor furniture. Thank you, Terrie, we have a terrific time!"

"This is now on our top 10 vacation lists. It is an outstanding location. The water quality is great, and there's a perfect little beach for the very little people. The house is rustic but has everything one might need. The variety of boats allowed us to see around the lake. We hated to leave."

"Nice loft. Had everything we needed. It had lots of little extras. Everything was very clean with only an exception of a pan that the previous guest had not washed completely. Overall it was very nice."

"Everything was good, except road noise was a bit of an issue. We closed the windows in the front of the house and that solved the problem."

"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"

"This suited us well for a 1 night stay. There were 4 of us. The twin bed I slept in makes noise every time I rolled over, so didn't sleep well. I have stayed in the vicinity before so I expected no cell service upon arrival, so just be aware and print the instructions to enter the home because you may not be able to get in on your phone. It's very small, but perfectly fine for us. I prefer dealing directly with the owner through VRBO instead of all the texts/notifications from Vacasa. That was...

"On arrival I loved the breathtaking views of the mountains ! The house was so spacious. Each kid had their own room and my husband and I loved having a master suite ! Our dog was so comfortable there as well ! I am really big on cleanliness and this house was immaculate !! We loved the hot tub! So relaxing ! I walked the dog around the house every morning and had noticed fruit trees ! The peaches were delicious ! Got Home from dinner one night amd we were getting of the car and a black bear...

"My husband, son and our friends enjoyed staying at this home. We all slept comfortably and had all of the necessary amenities. Hosts were very proactive and responsive. Appreciated the added touch they provided with the Vermont Maple syrup for our pancakes (I had actually forgot to bring syrup) and coffee. The group was able to enjoy the hot tub each night after a long day of skiing! Will definitely look to stay here again!"