Vacation rentals with outdoor seating in Berkshire County

This was the second time staying in this house with another family. Can't beat the convenient location to local mountains for skiing. House is spacious and plenty of room for two families of 4. Shiyrah is friendly and communicative.

We loved this beautifully decorated home. When we arrived the wood-burning stove and hot tub were already on! It was a very welcoming environment and very close to great barrington, MA and Hudson, NY. We would love to come back and spend either a winter or summer holiday here.

Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

My friend and I had a lovely two-night stay at Julie's place. The house is the perfect retreat—peaceful, cozy, and beautifully located. We especially enjoyed the evenings by the wood-burning stove and long, leisurely breakfasts on the porch while listening to the river. The beds were incredibly comfortable, with high-quality pillows and bedding—we both slept so well! I would definitely love to come back someday with my husband to enjoy the peace and quiet, as well as everything else the Berkshires has to offer. Thank you, Julie and Arthur, for sharing your wonderful home with us!

Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!

Beautiful space, super fun closet full of toys for the little ones. Amazing music and movie collections. Only critique is that there are a lot of ladybugs in the front bedroom, so if you have small children or hate bugs, just be aware that they might be there. Everything else was great!

We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay again.

The home was very clean and as described with everything we needed for our visit. Chris was very clear with his check-in instructions and quickly responsive to questions as we got settled. I would stay here again.

Everything you want in an Air-B-B . Clean and charming , right in downtown . We walked to restaurants every night. Lots of thoughtful snacks. Fresh Pint of whole milk and stick of butter in fridge. Host lived on site and was there to help with any situation. Great bedding and water pressure too.

Loved our short stay in this cozy space! Walked to downtown North Adams and Mass MOCA — I didn’t realize this Airbnb was so close until we arrived which was awesome! And the bed was sooo comfortable.

The place is a large upstairs apartment built into a single family home with a business on the first floor. Very Chester. Comfortable and warm. Everything was and felt clean, no worries there.

Was a very comfortable stay and host was great!

The stay itself was wonderful! As advertised, it was well within walking distance from the downtown area, was cozy, and looked exactly like the pictures showed. 5/5 stars What pushed it over the edge from a good Airbnb to GREAT, was the attention Jennifer paid to small additional details - little chocolates to welcome us, snacks intentionally set out for us, water bottles, and a few other things speak to how good of a host she is. 6/5 stars 5/5 stars for Jennifer and her lovely apartment, 3/5 stars for Airbnb: we didn't get a message from Airbnb until we were checking out that her messaging wasn't working, so a couple messages went unanswered. Jennifer had put her number in 3 different locations explaining this, so she was super proactive, we were just a little unobservant in seeing that.

Very happy with our stay at Frank’s in North Adams. Super friendly host and perfect place to enjoy a mixed bag of weather, mostly decent for early April, easy and content to both go out to see the city and just stay in to hang out in the three season porch or watch a movie. Great recommendations from our host for outdoor places to check out. Walkable. Peaceful. Would hope to stay here again

Melissa was a fantastic host. She was flexible on check-in and check-out and very generously lent us her snow brush to clean off our car after an unexpected and beautiful snowfall overnight. The area was exactly the peaceful, nature-filled escape we had hoped for. 10/10 would come back and stay here again - we were sad to hear we'd be one of the last stays.

This was our second stay and we just booked a third. This is the perfect location to visit our college student at Williams for concerts and events. The house is clean and comfortable and the hosts are perfect in every way.

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.

Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

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 always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

We've started here multiple times. It's a great value for the space and closeness to town. Elaine is a fantastic host - always friendly and responsive. Cannot wait to be back.

I cannot speak highly enough of Ephrat - she was a wonderful host and even let us stay later as we had family visiting. I had arranged a weekend for family and friends at this house, and she made the experience just as special as I had hoped for. On top of the stellar hosting and lovely home, the view is simply gorgeous. Best home to stay in during the fall in Great Barrington, hands down!

We spent a nice, early March ski weekend at this place - got lucky with the skiing and found the place ideal for our needs. Were traveling with a pet and the location was perfect from her perspective as well.