Vacation rentals with a hot tub in Pittsfield

We loved this beautifully decorated home. When we arrived the wood-burning stove and hot tub were already on! It was a very welcoming environment and very close to great barrington, MA and Hudson, NY. We would love to come back and spend either a winter or summer holiday here.

An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!

Terrific experience. Brandon responded right away to questions and was very flexible. We loved the house!

We booked this beautiful home for a girls weekend and it didn’t disappoint! ~10 mins from The Klocke Estate for a nice Friday dinner then stayed in the rest of the weekend! The kitchen island was our main hangout spot - played cards, completed a 1000-piece puzzle, made vision boards for 2025, cooked, ate, drank. We had the Sonos system going all weekend - built-in music in every room which kept the mood right. The living room was so comfortable for morning coffee and late night chats. Feels like you’re in a tree house! Beds and linens were all nice as well. Bathrooms spotless. We watched a movie up in the attic/loft TV area which was cozy. Hot tub worked well and we appreciated the shoveled pathway to get to it. All in all - a truly wonderful home which made our weekend really enjoyable!

We loved staying in your home. It was close to Mount Snow where we went skiing and we especially loved the fireplace and hot tub. The kitchen was so big and had everything we needed. Thanks so much for leaving the binder of instructions because it is important for us to treat your home like our own home and we want to do things right. We will be back next year. Tom and Stacie

Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.

Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

We had a wonderful time in Great Barrington. The house was close to town and other activities. We were with small kids and went to Tom’s Toys every day, and Ready, Set, Play in Pittsfield which was 40 min away. A highlight was the Norman Rockwell museum, about a 20 min drive. Gary was very responsive and the house met all of our expectations! The kids loved the playscape and trampoline! Would go again!

lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)

**Title: A Slice of Paradise at the Five-Star Serenity Resort** From the moment we arrived at the Five-Star Serenity Resort, we were enveloped in an atmosphere of luxury. **Accommodations:** Our suite was nothing short of spectacular. Spacious and elegantly designed, it featured breathtaking views, a private balcony, and a lavish bathroom complete with a soaking tub and rainfall shower. The attention to detail was impeccable, from the plush bedding to the locally sourced decor that added a unique touch to our experience.

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!

We had an amazing stay at this beautiful cabin in Vermont! We were there for a birthday getaway and couldn’t have picked a better spot. The views were absolutely breathtaking, and the cabin was cozy, clean, and stocked with everything we needed. We made a lot of home-cooked meals in the well-equipped kitchen and enjoyed relaxing evenings in the hot tub — definitely a highlight! Every detail, from the comfortable beds to the thoughtful amenities, made our stay feel special. Highly recommend for anyone looking for a peaceful and memorable escape!

This place matches its description perfectly. It is very secluded and all amenities are as described. Kitchen has everything you need and more. Surrounding area is gorgeous and easy to navigate. There are so many fun board/card games provided. The very cute town of Hudson, NY is a short drive away, and there are plenty of great little hikes around of varying degrees of difficulty. The hot tub works perfectly. Olivia was a delight to rent from - so communicative and all her instructions were super clear! Would gladly stay again.

Our stay in the Airstream was amazing! The cabin is beautifully done-up, with lots of thoughtful details like fresh milk and eggs from the farm. The hottub made our nights extra-relaxing, and having the farm to walk around and meet all the animals was such a nice way to spend a morning. Bring eyemasks though - the curtains are quite sheer!

Perfect for a winter getaway! The cabin was so cozy and comfortable, and the location is beautiful and remote. The hot tub was a huge plus and the host was incredibly friendly and responsive

This cabin is chic, cozy, and in a beautiful secluded location, such that you can take a dip in the hot tub listening only to birds. It's a true getaway treat. Highly recommend.

This place is a hidden gem in a great location, especially if you live ski or other winter sports (perfectly located close to several mountains). Regarding the property, it was pristine clean, well arranged and had everything we needed (or even more). The rooms were comfortable and the hot tub was a great touch. I would completely recommend this place to anyone visiting west mass, will not disappoint.

a very cozy cabin in a very quiet spot. made for a very peaceful getaway and they were friendly and informative!

We loved Ed’s home! Perfect stay making for a perfect weekend getaway.