Holiday rentals with a hot tub in Pittsfield

This is my family's second time staying at Nahuel's beautiful home. Our pup loves the fenced in yard, and my husband enjoys the hot tub + grill whenever he is here on a work trip in Kinderhook!

We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

The Art House suited our family history and reunion gathering perfectly. Our large group of 10 was very comfortable and there was plenty of room to gather, eat, and visit. The location was very convenient to shops and restaurants. The bedrooms are comfortable. Carl was very responsive both before and during our visit. I would definitely recommend this place for anyone with a large group visiting the Berkshires, MASSMoCA, Mt. Greylock or other local attractions.

Such a perfect house and a perfect stay! We did a midweek stay just to relax and couldn’t have had a better place to do so! The house is beautiful and so clean. The kitchen and everything you need to cook or grill (or make cheeseboards which is what we did). It’s super private and quiet and the back porch is the best. We loved having coffee on the porch every morning. Very close to downtown GB and plenty to do and see! Clear instructions and details about everything in the house and we got to check-in a little bit early. Hope to stay again!

My son and I had a great stay at Nicole’s place in Becket. We were centrally located to lots of what we wanted to see in western Massachusetts but also had plenty of privacy and quiet. We enjoyed fires in the fire pit, canoeing on the neighborhood lake, and swimming/playing at the neighborhood beaches. The house was full of thoughtful touches that made our stay easier… for example, extra towels, comfortable throw blankets, bowls and beds for our dog, snacks, and books full of local recommendations. Nicole was friendly and responsive both before and during our stay. I would highly recommend this spot!

What a gem! Reminiscent of lakeside “camps” that I visited as a child. We played games and did puzzles on the magical screened porch; comfortable beds, awesome showers, had the pond to ourselves and the dogs loved it, too.

We had a fantastic time! Lars was the best host imaginable and the residence did not disappoint either! Was the perfect getaway we were looking for!

Anthony's house was an excellent venue for the weekend of our son's wedding in Williamstown. It easily fit the eight family members staying there with plenty of privacy on three floors and great gathering spaces on the main floor, deck, and pool deck. We're grateful the pool was open; the kids loved it on a hot afternoon of our stay. If you are looking at this house, don't let the backroads approaching it look like a liability. They are well maintained and allow easy access to Williamstown and the southern Vermont towns along route 7, yet the quiet location will insure you sleep well.

Overall we had a wonderful stay. The weather wasn’t great but between the indoor pool and arcade there was enough to keep the kids busy!

My daughters and I really enjoyed our stay at Jacks place. The house is beautiful, and the surrounding private property is stunning. Nicole was very helpful whenever I had any questions.

The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.

Fantastic communication. Easy in and out. No complaints at all!

Gautam was very responsive and extremely kind! The property had a huge backyard. You don’t need to ever leave the premise. The pool, yard, and gazebo were the perfect place to spend the weekend. Each bedroom has a bathroom and had great privacy. It was a great weekend!

What a treat to stay at McCaela's magical, cozy, home! Everything – from the surroundings, to the furnishings, to the amenities – were just perfect. Entry into the house was no problem, and inside we found a delightfully thoughtful and intentional home that was extremely comfortable and spotlessly clean. Just as key, the bed in the primary bedroom was supremely comfortable! We had no reason to ask any questions, and we had no issues at all; still, McCaela reached out to make sure we were settled and to see if we needed anything. We SO appreciated her generosity, kindness, and insight into (and commitment to) the local community. It's clear that a great deal of thought and care has gone into this house, and we would stay there again in a heartbeat. The location is perfect – off the beaten path and extremely private, yet close to everything we wanted in the Berkshires. I highly recommend staying here, ideally for longer than the two nights we did. We can't wait to return!

My fiance & I really enjoyed our weekend getaway at this cabin. The space was perfect for just us two. It was very clean and exactly like the pictures shown. Our favorite part was the jacuzzi and the privacy it had. Also liked that it wasn’t too far from things. Would definitely stay again!

Really enjoyed our stay! Was perfect for our family to stay all in one place. Darin responded in a timely manner and was very helpful. Pool table was a great addition! Loved the location, it was beautiful & peaceful. We were disappointed we didn't see any bears :0) LOL

So much fun!! The airstream was super cool/relaxing and the animals were so adorable. Looking forward to coming back in the future!

The space is luxurious and stunning even more beautiful than the photos, so thoughtfully designed and really helped us feel at home at once. Matt and Sarah were so helpful whenever we had any questions. We had such a relaxing stay and feel so grateful to have been able to enjoy the space!

We had a great time here with our 9 month old baby. The pictures don’t do the house justice. Access to the lake for swimming and kayaking and the facilities (pools, beach, basket ball and tennis court) make this a great place for an active vacation. The house has everything you need to travel with a young child (toys, changing table, pack ‘n play and even black out shades). The towns of Athens and Coxsackie are a few minutes away and have decent food and drink options. We would love to come back!

Pictures don’t do it justice! The place is super adorable and relaxing. Great views and vibes. Personal touches that make you feel like you’re visiting a friends home instead of an Airbnb. Highly recommend!

We had a great time staying at Jessica’s place. It was a clean and beautiful space - perfect for children. The hosts were very responsive. Would definitely recommend for a family trip or a couple’s trip!