House vacation rentals in Berkshire County

We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

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.

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

What a spacious, luxurious retreat! My family and I completely enjoyed our stay in Prem and Mary’s beautiful home. Plenty of room to spread out and relax, high-end appliances, top-notch bathrooms and comfortable bedding all made for a happy and pampered stay. We loved sitting up late together around the gas fireplace on the enclosed porch and wow what a treat to have a grand piano in the house (haven’t played one in 30 years!). The house is perfectly located between the charming towns of Stockbridge and Great Barrington, with all the area attractions and restaurants, breweries, etc only a short drive away. Prem and Teagan, the house manager, were so friendly and helpful and responded immediately to any questions we had. Delightful stay in every way and we look forward to a return visit!

We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

Red Cottage is absolutely beautiful, a great space for a girls' trip! The surroundings are gorgeous, hiking trails are less than 10 mins away, downtown is 15 minutes away, but we spent a lot of time at the house catching up by the fire. The hosts were very responsive and helpful and provided us with tons of recs. We are already looking forward to coming back next year.

had a great family get together with our kids and grandkids! The space was perfect for all of us and a great location for skiing at both Bousquet and Butternut! Many restaurants in the area and kitchen well stocked for making family dinners. - easy access to everything - Thank you Jon for the use of your house - made our weekend great!

We had the most wonderful stay. Having traveled from Rhode Island for an escape from the holidays we had actually rented a hotel in Germantown initially. Without going into too much detail the hotel was not up to our standards. After one night there we began looking into alternatives. we found Hilltop and it looked perfect. Quickly, we were able to secure a booking for the remainder of our trip. Very responsive interaction throughout booking. It proved to be a peaceful oasis for the remainder of our trip and was a very memorable experience. The modern aesthetic was fantastic and we appreciated the architectural thoughtfulness which went into the design. It even snowed during our stay at the higher elevation the property is situated on. We were already planning a return visit to experience the surroundings in the summer. Thank you for sharing your place with us!

Very nice accommodations in a great location. A vehicle needed to get around to plentiful hiking, shops in nearby towns, and cultural sites. Very nice home for family gatherings and with all necessary amenities.

Josh’s was the most charming of all the Berkshire bnbs we’ve rented so far. His historic home has a well-stocked kitchen, comfortable beds, quality linens and a living room with plenty of seating for 8 or more to comfortably lounge in front of the huge stone fireplace for board games and movie nights. The interior of this late 1700’s home was spotless and decorated with a stylish combination of contemporary practical furniture as well as several groupings of that suggest how you might unwind: write a letter at the secretary by the window upstairs, put your feet up and read at any number of antique armchairs strategically placed around the home, or challenge your kids to a game of mini-billiards. We had a few questions during our visit and Josh was friendly, helpful, and quick to respond. The grounds have walking paths and the location can’t be beat: close to the grocery store and downtown Lee while still feeling private. It was the perfect spot for us to unplug. We’ll be back!

We had a wonderful long weekend at Elle’s house. The bedrooms and living spaces were thoughtfully laid out and decorated beautifully. A short drive to lots of little cafés and hiking trails. We appreciated the quiet solitude of this little getaway in the Berkshires, and the ping pong table too. We didn’t get to use the lake (snow in April!) but hope to return to try again!

Had a great stay here this past weekend with a group of friends. The space was very clean, and the fenced in yard was perfect for our dog!

Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!

Nancy was a great host. She was responsive and proactive providing us instructions for accessing the property. The house had lots of space for our group of 9 and it was nice to have a full kitchen to cook in while we stayed. The walk to MOCA was around 15 minutes with our group, which included five kids. It was nice being so close to town. We hope to be back again!

Beautiful, clean and great location! We were up skiing at Catamount so the location was ideal, and the sauna was a nice treat everyday. The house is beautifully decorated and spacious and open. There are a few different levels so plenty of room to spread around with a separate spacious TV/exercise/bunk room in one of the levels. The 2 king beds and twin beds in the bedrooms were all very comfortable and each of the bedroom had their own bathroom next door. The kitchen is fully stocked with kitchenware and necessities/spices etc. Kids went sledding and we even hiked up several times to the top of the hill with great views. Carolyn was very responsive and accommodating.

What a find! Jeff's place is sparkling clean, super homey, and located on the edge of a beautiful forest with a swimming hole nearby. Bedrooms were great (they set up two extra for us because we were four individuals) although the set up would work well for couples. Kitchen has basically everything you'd need. The living room is great for watching movies. The bathroom upstairs also has a tub with a great view - overall, we loved the place and location!

Just had a great stay in Great Barrington. Enjoyed the house and all of its amenities. Location was great, close to great restaurants, hiking and skiing. Would recommend this property and our host!!

the airbnb is very homey, well stocked, and easy to navigate. we had one slight issue with a mess that was not found by the cleaning crew, but robert was friendly and shared our concern about this.

Yina’s place is absolutely beautiful, clean, and surrounded by lovely scenery—truly worth the stay. From the coffee she chose to the shampoo and body wash, I enjoyed every little detail. Yina is a very responsive and responsible host. I really appreciated her quick replies and thoughtful touches. Would love to come back again!

fantastic and cozy, nice backyard, well equipped with amenities as well

Lovey home and very convenient location in Willamstown. Would highly recommend.

We had a wonderful stay at Anna's place! It was our favorite of the three places we stayed in Massachusetts -- so comfortable but also interesting and charming, which can be a hard combination to pull off. The house had everything we needed for our stay and the hosts also left some lovely extra touches that made us feel so welcome as guests. The area is so lovely that we hope to have the chance to come back someday when the leaves are out and would definitely choose to stay here again if it's available!

Wonderful space and location! Mattí was responsive and friendly, and provided helpful info before and during our stay. The house is beautiful and walkable to North Adams. Loved it.

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!