Vacation rentals with a hot tub in Pittsfield

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!

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!

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 really can’t say enough about Jackie’s place. Beautiful and peaceful surroundings. The home is well appointed and comfortable. The place is so nice we actually cancelled our plans for Saturday night just to stay in and enjoy the vibe. Spent part of the evening just relaxing in the hot tub looking at the amazing night sky!! The kitchen had everything we needed to cook dinner and a nice selection of pots and pans. Would highly recommend. Jackie was very responsive and easy to reach.

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!

Lucas did everything to make our stay at the Hillside Hudson home wonderful. He was extremely responsive and professional and willing to help when we had an issue getting in the front door. Thankfully, the back door was open when we arrived late in the evening on our check-in day. Connecting to the wifi was seamless, my entire party was able to work remotely with no issues. Kitchen is stocked and a great space for home cooked meals. However, there are no oven mitts, we would definitely recommend getting some of those! We enjoyed the deck during sunset and sunrises as nothing beats this view! Lucas gave suggestions on things to do and restaurants to visit. Everything was as mentioned in the airbnb description. Would 100% recommend for others to book at this scenic and private getaway.

My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

The Batwing is the perfect spot for a big ski group. Can’t get any more convenient. House was clean and comfortable. Beds were super comfortable. Double sided fireplace was awesome. Hot tub was awesome. Had a great layout and the host was super responsive. Would 100% stay there again.

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!

We absolutely loved our stay here! Darin’s house and property are wonderful. The cleanliness, attention to detail, privacy, quiet, amenities- everything was perfect. Our two children - 2 and 4 years old loved it as well. Darin was always responsive with recommendations and answers to any questions we had. The location is perfect- close to numerous trails and cute restaurants. Thank you so much Darin! We can’t wait to come back :)

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!

AMAZING! Some friends and I escaped the city for 3 days and stayed at this cabin. We will definitely be returning. The place was huge and so cute. Joy was more than accommodating. The hot tub was huge and clean. The wood burning fire places were so cute. Overall amazing place to say I would 1000% recommend.

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.

A charming cabin perfect for a weekend away. Our group opted mostly to stay in instead of explore local areas and it was the perfect size with just enough to do! The small explorations we did have for local coffee and produce were wonderful. A couple issues with some household appliances but the host was responsive and considerate to resolve them. Loved the doc, kayaks, and hot tub as well as smaller objects to use for entertainment, such as a guitar, fireplace, and games. Hope to come back next year!

We had a wonderful week once again at this beautiful, cozy cabin. It is always spotlessly clean and comfortable. Adam and Filipa are exceptional hosts - very kind and responsive. The location is perfect - easy to get into town to enjoy restaurants and to ski at Mt. Snow and even though we got a lot of snow and ice the driveway was plowed and sanded to make it safe for travel. I highly recommend this home for your trip to Southern Vermont. I can't wait to return!