Vacation rentals with a pool in Berkshire County

We had a lovely time with our family! We were with 2 young children and my elderly father who cannot walk well (uses a walker). The house was perfectly designed to accommodate my father and had great living areas for us to spend time together. A very cozy, warm and welcoming home (with lots of amenities!). Yael is a very friendly, responsive host. We’d gladly come back for another winter or perhaps a summer stay! Thank you Yael!

We loved staying in this beautiful home. We were here for a college reunion, so well situated in the Berkshires. The home was quiet and private, the pool was amazing, and the space was incredible. Most of all, the thoughtful amenities - children’s toys, movie theater, swim toys - were very appreciated. The owners were very receptive and responded right away to questions, and all in all it was a most wonderful place to be!! Thank you!!

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

I think this is the most beautiful air BNB I've ever stayed at. The property is super big and perfect for families. There are a ton of bedrooms and bathrooms and the living area is so beautifully decorated. The kitchen was well stocked and really modern. There's tons of stuff to do right in the home so you don't have to venture away, but if you do you're very close to everything you'd need. The pool was pristine. There were gorgeous fire flies putting on a show for us every night. The view was incredible. We even saw a rainbow on our last day. It was peaceful and private. I highly recommend this place and the hosts. They were super responsive and went above and beyond to accommodate us when we were dealing with some car troubles. Thanks for the incredible stay!

We had a wonderful stay at this Lake Pontoosuc property! The house was spacious, spotless, and beautifully maintained, with amazing lake views from the deck. We truly enjoyed the wide range of activities available: kayaking on the lake, playing cornhole, relaxing by the swimming pool, and ending the evenings around the bonfire by the water under a sky full of stars. Inside, the kitchen was fully equipped for home-cooked meals, and the cozy living room made for perfect family gatherings. The bedrooms were comfortable and roomy, and the entire property, including the lovely garden, felt incredibly welcoming and well cared for. The only minor issue was the WiFi, which was a bit spotty—worth noting if you’re planning to work remotely. But it also helped us unplug and enjoy the experience. We highly recommend this Airbnb to anyone looking for a peaceful yet fun-filled lakeside escape. Jay and Stephanie were very helpful and accommodating. We’d absolutely love to come back!

This was our second stay at the Queechy Lake house and it did not disappoint! The home is wonderfully maintained, fully equipped and cozy - we appreciated the new additions of the pool and backyard activities. It rained most of the weekend but we utilized Meredith and Jason’s local recommendations and had a blast.

Stayed here with three others for work. The house was clean and well updated. We had no issues and will look to stay here again.

Thank you for a clean and comfortable stay! We were in town visiting family and this was an ideal central location. The pool was a fun addition for our kids plus we were able to turn on the heater ourselves with no issues. Property was exactly as described and it had almost every kitchen gadget for the home cook. There was even a well organized drawer of glass storage containers. Convenient and thoughtful! It’s always quiet and peaceful whenever we visit the Berkshires and this trip was no different.

Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!

Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!