Vacation rentals in Pittsfield

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

Home was beautiful, clean and close to Jiminy Peak, 16 minute drive! Great kitchen and living area to hang out

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

Aline & David provided a great space for my friends and I to have a an eventful, weekend getaway from the city. Amazing location and truly a home where you can have a great experience regardless of the weather. The game room and personal lake are the unique, finishing touches to this home.

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

Lockwood Lodge is a beautiful and peaceful place in a perfect location. Our families loved watching the snow come down from the big windows, the view is spectacular. Our kids loved the vintage video game consoles, the grownups loved the records and games/puzzles, and we all felt right at home in the lovely house. It was a perfect spot to hunker down in the snow storm. Jeremy was incredibly responsive and thoughtful and did much to make sure our stay was perfect. We hope to visit again in the summer to take advantage of the pool, which must be really special against the backdrop of that view.

Walkable to everything in Williamstown; clean and comfortable; well-appointed kitchen. We enjoyed our stay, and we hope to return in future.