Holiday rentals with a hot tub in Pittsfield

We had an amazing stay at this home! My girlfriend, our dog Barry, and I spent a long weekend here and absolutely loved it. We made great use of the hot tub, played in the snow, and enjoyed cozy evenings by the firepit. The starry night sky was breathtaking, and the location was perfect—just a short drive to the grocery store and the charming shops of Red Hook. We highly recommend this place for a relaxing getaway!

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!

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.

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.

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!

great stay minutes from mount snow hot tub was great would book again in a heart beat

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.

I genuinely can’t say enough about this place. It’s absolutely beautiful! Thoughtfully designed, super clean, and filled with the kind of details that make you feel at home. The plants throughout the space add such a calm, lived-in vibe, and the views are unreal. The outdoor areas were perfect for lounging while it was warmer (we visited mid April) but it’s definitely a spot you can enjoy in any season! The bathrooms and appliances, the WHOLE place is all super modern and brand new, but still feels really cozy and welcoming. And the host are truly one of the best we’ve ever encountered. So kind, so responsive, and even sent over local event links to help us find cool things to do in the area on Easter Sunday! We’ve stayed in a lot of Airbnbs over the years, and this one is easily in our top 5. Zero regrets booking it and we’re already looking forward to coming back!

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!