Vacation rentals with a pool in Great Barrington

We stayed here for about a week to getaway away from the city and we absolutely loved it! It was the perfect place to recharge and relax. Everything was as described!

Kelsey is flexible and responsive. You can tell she thought about how to curate a great stay by all of the amenities and presentation of the house. It’s cozy! Kelsey does have house rules but they’re not overbearing and if anything it was nice to have clear expectations communicated from the beginning.

I had a wonderful stay at this Airbnb! The space was incredibly clean and well-kept, and the view was absolutely beautiful, such a peaceful and relaxing spot. Rebeccas and Aaron were very responsive and friendly, which made the whole experience even better. I’d definitely recommend this place to anyone looking for a comfortable and scenic getaway. Would love to stay again!

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!

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.

⭐️⭐️⭐️⭐️⭐️ Perfect Stay for Two Families with Young Kids! We had a fantastic stay at this Airbnb with two families—four adults and four kids under the age of 6—and it couldn’t have been more ideal for a group like ours. The house was spacious, clean, and thoughtfully set up for families. There was plenty of room for everyone to spread out, and the layout gave each family a bit of privacy while still offering great shared spaces for meals and playtime. One of the highlights for the kids was the stash of scooters that kept them entertained for hours—such a nice touch! Just a heads-up to future guests: be sure to bring helmets for your kids, since those weren’t provided. For the littlest traveler in our group, there was even an infant bouncer, which made things so much easier for the parents. The kitchen was well-equipped, the big dining table fit all of us comfortably, and there was a safe outdoor area for the kids to play. Plus a hot tub!

The Soapbox was a delightful house for a two couple weekend getaway. We appreciated the privacy of the house, the relaxing fire pit and hot tub, and the convenience of being only a short 10-15m drive from anything in town. Communication was straightforward and quick, and the house was well stocked with all sorts of glassware and cookware for meal preparation.

Jacquelyn was an amazing host - she was very flexible with our party and responsive to ensure all of our needs were met. The house is beautiful inside and out and even though the weather did not hold it was cozy enough inside where we still managed to have a very relaxing weekend. The rooms are exactly as pictured and would highly recommend staying here. We hope to be 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.

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.

My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.

Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

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!!!