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

Our stay at Michael’s AirBnB was everything we needed! The property was easy to get to, secluded, and conveniently located to nearby stores. We brought our 3 dogs and the big yard was perfect for them. Highly recommend for anyone looking to unwind.

This was my dream tiny home! The layout made it super comfortable for two adults, two teens, and a medium sized dog. Beautiful design and WOW the location! Right on the lake and close to cute towns with shops and hiking. Not to mention the FREE breakfast and lunch at the locally owned general store. Christopher went above and beyond good hospitality. We loved the hot tub, super clean and private, the fire pit was great as well! We plan to return in the summer so we can enjoy the lake access more which was so beautiful to watch the sun rise over it in the morning. I would just suggest if you use the pull out sofa bed it’s probably more comfortable for younger kids- my 12 yo was fine but my 15 yo was not super comfortable. We would prob bring our mattress pad when we come back but not a big deal. Still totally worth every penny and more. Make sure you take advantage of this great tiny home!

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.

The house is very cute and can easily accommodate 6 people. The kitchen is well stocked and we enjoyed making meals for the 6 of us. Andres was quick to reply to any question that we had and solve any (minor) issue that we encountered.

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.