Holiday rentals with a pool in Great Barrington

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 had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

My friends and I had such a great stay. Everything was as described. The house was very comfortable and well equipped. We just wish we could have stayed longer!

This place was an absolutely dream!! We were here celebrating with a group of friends- the space was comfortable for a group of 10, well equipped for cooking meals, and had so much charm. We didn’t want to leave and are already looking at when we can return next year. Truly the perfect upstate getaway!

We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come back!!

My brother and I spent an amazing weekend at Natasha & Vince’s peaceful lakeside home. The house was clean and roomy and the location was perfect with easy access to the lake for fishing and swimming during the day and beautiful sunsets at night. A lovely home with kind attentive hosts!

The pictures don’t do the property justice. We had the most amazing, peaceful stay. The heated pool and hot tub were everything. And even when it was raining, sitting on the porch was so inviting and relaxing. The interior is just as gorgeous as the grounds, so thoughtfully decorated and stocked, made us feel right at home. I only wish we had booked it for longer. We will definitely be back.

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.

Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.

Hamilton is a wonderful host and the area is always beautiful and fun.

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!

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!!!

We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!

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!

Beautiful property. We enjoyed very much the tranquility. There was an issue with the kitchen light but maintenance was going to address it. The exterior of some of the buildings needs to be worked on, but overall the place was great.