Pet-friendly vacation rentals in Berkshire County

This cabin was an absolute dream come true and exceeded all my expectations! From the moment we arrived, we were enchanted by its charm and the serene beauty of its surroundings. The cabin itself was impeccably clean, cozy, and wonderfully decorated, making us feel instantly at home. Every detail seemed thoughtfully considered, from the comfortable furnishings to the well-equipped kitchen. We particularly loved the personal touches in the decor, i.e. the writing on the walls and all of the books. The location was simply perfect – as a city gal, being surrounded by nature in a peaceful setting was exactly what I was looking for. I enjoyed spending time in the yard in the morning with my breakfast and enjoyed driving to the Norman Rockwell Museum. Taryn was incredibly responsive and helpful with any questions I had and made the entire booking and check-in process seamless. We left feeling completely relaxed, rejuvenated and already have our next stay booked! This place is a true gem!

Our group of 5 were very happy with our stay in Lenox. Location was perfect in that it was close to everything we had planned in the area. Everything went very smoothly in booking the rental and all the communication involved. The place was very nice.

Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.

Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!

Jaclyn’s home is the perfect place to get away and relax. Being on the water with a wood burning fire place was absolutely lovely. The home was clean, well organized, and Jaclyn was always responsive when we had a question. The home was an easy 20min drive to a lot of fun small towns. There was a little traffic noise when we were outside from the highway, but it was peaceful otherwise

We stayed at Caroline and Nathaniel’s beautiful home over the winter and celebrated NYE’s. Their house is beautiful and perched on top of the hills overlooking a lake. The view is absolutely stunning in the mornings. The house was well maintained and clean. The hosts were very active in communicating with us where we needed anything or if we needed to be aware of any situations regarding the house. I would definitely stay here again.

This is a great stay! Peaceful and you feel as if You are one with nature. Very clean. Arthur and Julie are quick to respond. Kitchen and bath have everything you need, including starter and wood for the wood stove. Cozy place right on the river where you can listen to the rolling sound of the river. Close to CT where we had a nice dinner at an old Inn with delicious blueberry cobbler. Beautiful Drive to norman rockwell museum, great Barrington and other Berkshire towns. We would most definitely stay at this home again.

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

We loved staying in this beautiful home. We were here for a college reunion, so well situated in the Berkshires. The home was quiet and private, the pool was amazing, and the space was incredible. Most of all, the thoughtful amenities - children’s toys, movie theater, swim toys - were very appreciated. The owners were very receptive and responded right away to questions, and all in all it was a most wonderful place to be!! Thank you!!

Beautiful, cozy accommodations. Comfy bed. Upscaled shower products. Wonderful towels. My husband said great coffee! The pool was inviting, but the weather was not cooperative while we were there. The actual space in the room is on the smaller side, but cozy enough for us two and our cockapoo. It was ultra convenient to our daughter’s house only 10 minutes away. We were there for family time but great recommendations for the area were given.

Melissa and Geoff's place is in beautiful surroundings and well within a short drive to excellent restaurants, museums and outdoor activities. We were there during an especially rainy and cool period, but the apartment kept us toasty and warm after a day of dodging the raindrops. The king size bed was lovely and a white machine lulled us to sleep. The deck attached to the house was wonderful and when the weather looked as if the blue skies were here to stay, Melissa asked if we wanted dry cushions for the chairs- just a lovely thought. The gardens were just beginning to bloom and the property is spotless. We will definitely return to Sweet Dreams; the apartment was a pleasure to be in. Andrea and Ray

The pictures don’t do it justice. A beautiful place for a peaceful retreat. The home is well equipped with everything you might need and more. And the decor! The more you look the more interesting the space gets. We loved our stay.

We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come back!!

We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay again!

Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.

Teva’s place is exactly as described! He was a very responsive host and had great recommendations on things to do/places to see. The house is very private and quiet and surrounded by nature. This house has been one of the better stocked houses that I’ve stayed at before and had something for everyone in my group from babies to adults. I would recommend staying here for a relaxing weekend away! A surprise bonus was watching bears cross the driveway almost everyday (from the safety of inside)!

Amazing place, incredibly clean & an even more incredible view. Loved it!

Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

Rachel’s carriage house is a charming and beautifully maintained property—just as described and shown in the photos. Even though the weather wasn’t ideal during our stay, we thoroughly enjoyed cozying up and relaxing in the warm, inviting space. One of our favorite features was the natural light streaming through the tall paned windows in the kitchen and dining area, overlooking the garden—a perfect setting for our morning coffee. The carriage house was thoughtfully stocked with everything we needed for a comfortable and restful getaway. It’s clear that Rachel has put a lot of care into creating a welcoming experience for her guests. We truly enjoyed our time in the Berkshires and would happily return!

We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!

Fintan’s place in the Berkshires is a great find - it was immaculately decorated, with thoughtful snacks and drinks upon arrival, and location was a perfect less than 10 minute walk to charming Great Barrington. Both Fintan and his partner were also super responsive and welcoming! I highly recommend their place.

Its a lovely airbnb..and a great location so close to many towns. We went to Tanglewood one night and it exceeded our expectations. I only wish we could have stayed longer. And such a gorgeous yard!!

Nicely appointed and updated cottage for a quiet weekend get-away. The hosts think of everything, in terms of supplies, kitchen set-up, and nice decor. I couldn’t find a kitchen item and it was delivered quickly, which was very thoughtful. Bed was super comfy and the a/c window units came in handy! A little bit of road noise during the day, but it’s not bothersome. Wish I’d been there in a season to enjoy the local town beach, which looked nice. Definitely recommend!

The property was as described, beautifully situated by the water in a beautiful location. Lee, the host, provided prompt and responsive communication. the unique outdoor shower and toilet (incinerator toilet) were acceptable for us, but the space was somewhat limited for two adults and two children; it may be better suited for two guests.