Search Vacation Homes in Pittsfield

"See you again next year ! Thank you"

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

"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!"

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

"Great little cabin - really enjoyed our stay"

"Our stay was very enjoyable. We had teens and grandparents in our group. The teens loved the water activities and the grandparents enjoyed viewing from the fabulous deck. House is very clean, has everything you need and views are incredible. Perfect lake house stay!"

"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."

"A group of 8 of us came to my daughter's graduation from Law school from Friday to Monday. It was such a great way for all of us to interact. The house was fantastic! Spacious and clean and updated and modern. This was my first time doing it up line this vs hotel rooms. I will always use VRBO for our groups from now on. Everything was EXCELLENT!!!"

"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!"

"Location was perfect to the mountain, easy to find and very comfortable! Hosts were responsive leading up to the visit and super helpful!"

"All good lots of fun"

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

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

"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."

"Was a great place to stay. Location was awesome and house was clean. Would definitely stay again."

"Our ski group reunions look a little different these days with little ones, but this house is perfect. With two floors and private bedrooms for all, we has 12 adults and 3 small children stay comfortably. The communal space is awesome with a long table for "family" dinners and socializing. Two refrigerators is clutch with such a big group and the proximity to killington skyship and bear mountain lodge make it SO easy to have a group of skier/non-skiers without being too far away. Loved the...

"Irina was a lovely host and her house was a great spot."

"Lovely stay w lots of common space, nearby to okemo"

"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."

"Will be back!!"

"Wonderful cabin with every detail provided. We felt pampered and relaxed immediately. Perfect location for everything from hiking, swimming to skiing"