Holiday rentals with outdoor seating in Berkshire County

A beautiful serene home set up with everything you need. We loved the space, both inside and out. There was a country store right down the road that had amazing food. Enjoyed relaxing on the deck after a great day of hiking. With so much hiking in the surrounding area, we are already looking forward to booking again.

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).

This was our second stay at Mary’s and we hope it won’t be the last. Her house is beautifully appointed, peaceful, comfortable and amazingly clean. (It remains the best stocked Airbnb kitchen we’ve experienced for acid cooks!) It’s very well situated for visiting many charming towns in the Berkshires as well. Mary was wonderful with us - sharing items from her garden, offering great recommendations on places to visit and eat - while also being conscious of letting us just relax and enjoy her house. A+

Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.

We loved staying at Carolyn’s place. It was just how the listing and photos described: clean, private, had plenty of amenities, etc. Carolyn was quick to respond to questions, and graciously let us return after checkout to retrieve something we had left behind. Would highly recommend this place if you are looking to stay in the berkshires!

We had a good time, and the lake was very nice. Thank you!

Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Fantastisch!! Charming, comfortable, quite and close in. Love this old house with beautiful woodwork, kousa dogwoods in full bloom in the yard. Great stocked kitchen, although we ate out at the many yummy cafes and restaurants. Mooncloud was a favorite! Comfy, spacious living room. Nice large dining table. Trice was a wonderful host, quick to respond and let us enjoy our space! I am so glad I took a chance on airbnb again - this was one of my favorite stays on airbnb and my favorite in Great Barrington! Would definitely book again!

Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

Went for a Berkshire School reunion the two of us, perfect spot. Charming quiet grounds, perfect location for accessing Berkshire School, clean, Keurig, comfortable bed, amenities as stated (and quick confirmations from host), super easy process for check in and check out. Asked many questions and host responded very quickly and was very friendly in her communications.

We enjoyed our stay at Tom's place. It was spacious, well appointed and clean. The birds and squirrels in the nearby trees were entertaining. The location was excellent for exploring North Adams on foot and nearby towns/parks. Tom was helpful and responded quickly to all our questions. I would highly recommend staying here.

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!

Perfect place to stay while enjoying Great Barrington and the Berkshires.

Great spot, very well-appointed, with beautiful views. Frank was a great host and I highly recommend.

Brent's place was everything we were looking for! We were hoping to have a cozy base to explore Mt. Greylock, Mass MOCA, and Williamstown, and this spot couldn't have been better. Plus, the property itself was fantastic -- spacious, incredible views, and a wonderful outdoor kitchenette/sitting area. Brent is also a very responsive, very nice host.

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!!!

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!

Elaine’s place was absolutely perfect for what we needed; which was a comfortable, clean, private space that was close to a show we were seeing at the Mahawaie Theater. Only about a 5 minute drive, which Elaine assured us it was. Space was very private, with own bath which is important to us. Very clean, bed nice and comfy. Had refrigerator, microwave, coffee pot, tea pot, as well as coffee and tea !! Plus creamer in fridge. Would def recommend.

A great place in a beautiful location. We had a blast at the adventure park and exploring western MA. Kids are already planning our next trip back.