Search Holiday Homes in Pittsfield

"See you again next year ! Thank you"

"Great place to unwind. Very quiet and excellent view"

"Really enjoyed our stay. Beautiful location and truly relaxing"

"Good stay. Lots of bedrooms and a large living room. Host was very easy to contact."

"8 people. Good home layout for people to be together and separate at the same time"

"Nothing but positive things to say about the house. Would stay there again."

"Listing details were accurate and house was very impressive upon arrival. Would love to stay at this property again! The onsite contact (Tanya) was very helpful with questions too."

"Our stay was perfect! The house was clean and well prepared for our arrival. Close to town and campus. Hosts were very responsive to our one question! Thank you!!"

"This was hands down the best host I have ever encountered. Incredibly accommodating and so responsive. The property was well appointed right down to the nice soap and towels in each bathroom. It felt like you were staying at a family members home. We did lots of cooking and grilling and had everything we needed. Couldn’t have asked for a better place to stay. We didn’t want to leave and look forward to another trip! Thinking already about when we can come again next. Thank you so much!"

"We loved our stay. There were plenty of beds and bathrooms for our family. The kitchen was the most well stocked kitchen ever. Better than being at home even! Really loved the porch area for storing ski gear. The hot tub felt great. Loved all the windows. So much light and great view. The only small draw back was it’s not a true ski in ski out. The trail is close but you do need to walk a bit to get to it. Overall we had a great visit and would stay here again!"

"This rental was not only clean and roomy but in a great spot. It was spacious throughout and the beds were comfortable. The backyard and hot tub were very nice too.. I would definitely stay again!"

"We loved our stay here. Only 18 minutes from killington. The house was clean and cozy. I’d definitely book again."

"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"

"The house was really quite great - especially for a winter getaway. It had everything you could possibly need and then some! My only critique was how difficult it was to communicate with the host. It feels very automated and difficult to get even the simplest answers."

"What a great house! We had a large group staying while we participated in an event at Pico. It was perfect for us. Close to the mountain, lots of room, inside and out. John was a wonderful host, very attentive and responsive. Thank you for a memorable weekend!"

"Bob’s bungalow was a perfect homebase for our ski trip. It had all the necessities we needed for cooking sleeping, and just plain hanging out after a long day of skiing."

"The location was amazing! Communication with Ryan was great. He was super responsive and very helpful."