Vacation 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 had a lovely stay at Elizabeth's place. The house was big enough for our large group, the kitchen was well stocked with anything we might need, and the area was peaceful and beautiful.

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+

Nice spot for a short getaway. Enjoyed the canoe access and paddling around the beautiful lake. Clean accommodations, AC, and comfy bed. Very close to Great Barrington.

beautiful well maintained house, supremely functional as well as spacious. very clear instruction all over the house. 5 bathrooms to go with each of 4 bedrooms. multiple lounge areas. fully equipped kitchen with anything once could need.

Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!

A perfect location nearby to the wedding venue we were attending! House had everything we needed to feel right at home. Very clear instructions and a beautiful spot. Wish we could’ve stayed longer!!!

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!

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.

Larry and Lana were perfect hosts. Very welcoming and helpful with local advice. There's a lovely walk around their property- just under half a mile so great to stretch early morning legs.

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

Great place to stay and the owners are super friendly! Highly recommend and we’d love to come back.

I’ve visited many, many AirBNB’s over the years and Elisabeth and Ricky’s was one of the best. The accommodation is beautiful, it’s a lovely little converted flat above the garage, settled into the woods and garden. We were greeted by their corgi and by Elisabeth who both made us feel at home. We were able to wander their gardens, drink gin and tonics in the sun and generally make ourselves at home. A lovely couple and a highly recommended Airbnb.

This was a great location for some hiking and a concert at Tanglewood. The house is well equipped, including water and snacks (much appreciated). The host is friendly and proactively communicative.

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

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.

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!!!

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.