Holiday rentals with outdoor seating in Great Barrington

We appreciated the many amenities of Edward's place. Clean with comfortable beds. Loved the Master rain shower. Amazing, comfortable upstairs suite. Great washer dryer (upstairs). Fenced yard was a good size for our border collies. Sweet Pea's diner in Hillsdale is great, with a broad and varied menu with some creative options and great pies! Don't miss the beautiful park, Roeliff Jansen, a bit further down the road from the diner (8 minutes from house). Lots of walking trails with scenic views of the surrounding mountains and a great creek for dogs to play in. Visit the unique Book Barn and beautiful waterfalls: High Falls (Philmont) and Bash Bish Falls (Taconic State Park).

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

We had a great time, the location is great, right on the water and the fishing was even better. A very quiet lake and much bigger when you are out on it in the kayaks. I would surely stay here again!

Erin’s place was absolutely lovely! We really enjoyed the location - so peaceful and conveniently close to Art Omi. The cabin was beautifully maintained, and we especially loved the interior design, which felt both stylish and cozy. We stayed for two nights but honestly wish we could have stayed longer. Highly recommend!

We really enjoyed the our girls weekend in the Berkshires! The house had plenty of places to sit and hang out, which was especially useful because it was a rainy weekend. The house is in very private and in the woods, and was great for bird watching. It is also very close to Great Barrington with lots of restaurants. We would definitely stay again!!

Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

For our fourth stay at Katie and Greg's, we were just as satisfied as the first x3 trips! And we're already planning our 5th! Truly a gem of a home and wonderful hosts. Highly recommend!

Staying at Hawthorn was a special treat. The house was cheery in the midst of winter and felt like home! Centrally located in the Valley with easy access to Hudson and venturing out further, exploring local markets and sweet little helmets! The perfect get away

Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

Loved this little apartment. It has everything you need and more.

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!

Cute room above the brewery was a nice get away for my wife, our little dog, and I. John was friendly and so were all of the other employees and guests. The Irish band was great and the patio by the brewery was very cozy the beers were also delicious too. The room itself was spacious and well furnished with a good size bed and additional day bed. Fun weekend get away for all ages.

We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

Had a quick but great 1 night stay here on a visit to see Mass MoCa. The place was perfect - clean, close to the museum, etc. And Matti was very responsive as a host as well as respective of our privacy/space. And definitely leverage the guidebook they created - excellent recommendation on restaurants!!

Definitely a space with great level of thoughts and details makes you feel comfortable and relaxed. Surrounded by the nature, you can immerse yourself in the beautiful mountain view and bird chirps, very peaceful and tranquil. We saw deers walking by, rabbit hiding in bush from raining, and a little chipmunk busy around the house all the time. Thanks Katey for sharing her beautiful home and being a great host, super responsive and provides lots of useful information. We had an amazing time!

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

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.

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

I had a great stay! Super comfortable bed, room had everything I needed, and the AC unit kept my room very comfortable on the 90 degree day! Henry & Jorge were both very kind and easy to be around. If you're looking for a comfy bed in a comfortable space, this is perfect!

Always an easy peaceful stay whenever we stay at David’s place. We will be back again

Luke is a great person with an amazing personality. If you have any questions, just communicate with him and he will take care of everything else. Have a bless day everyone!!

Great stay for skiing at Jiminey Peak! We would definitely stay here again. Clean, spacious, great location and reasonable price!

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!!!