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 stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

Cozy home, with a very nice kitchen / dining room to gather in. High ceiling, warm lighting, and a few thoughtful antiques/decorations. Great place for evening games after a day on the slopes!

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!

My girlfriend and I spent four nights days at Joe and Jess’s beautiful home for a much needed vacation after the holidays. We spent most of our days/nights in the sunroom playing board games and watching movies with the beautiful view of the lake. It snowed halfway through our stay and the snow on the lake made it truly feel like we were in a winter wonderland. The house was very clean and we had everything we needed to cook our meals. We would love to come back during the warmer months and explore the lake as well as some of the hiking trails nearby.

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!

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.

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.

Spacious stay, wonderfully clean and quiet and an excellent view from the balcony. Lots to see and do in the area. It got a bit cold in the bedroom at night - advise packing some warm pajamas if traveling in the colder seasons!

Very cozy apartment in a great location between Pioneer Valley and the Berkshires.

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

My husband and I had a wonderful stay. We loved the comfortable feel and all the tasteful touches of this apartment. The view of the landscape, especially the pond in the distance was beautiful. I stayed one night longer than my husband, so I can say that the accommodations are great for one or two, very safe feeling. There are many hikes and walks in Colombia County. My favorite was a long walk around the pristine lake at Taghkanic Lake State Park, a mere 30 minutes down the Taconic. Worth the drive this time of year - very few other people and a beautiful place - highly recommend. Melissa was very easy to reach as necessary and very pleasant at every encounter.

The apartment was a clean and cozy space near Williamstown and exactly as described. We appreciated the flexibility with check out.

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 had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

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.

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'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.