Pet-friendly vacation rentals in Berkshire County

Beautiful space to cozy up and enjoy peace. I needed a mental health getaway to enjoy nature and respite from the day-to-day. The wood-burning stove was incredible, already set up with everything I needed, ready to have a fire. The fully functioning and easy-to-use kitchen was great, and there were beautiful paintings everywhere. Be mindful if you have a dog—I did see a bear down the street about a mile away, which is expected in Western Massachusetts, so keep pets leashed. As described, the house connects to an apartment on the other side, with a door leading to their porch through one bedroom, and a window in the other. Vintage cabin vibes inside. Beautiful views no matter which way you look. An enormous and diverse selection of books, old and new. I stayed one night and wish I could stay another. My lab enjoyed relaxing by the fire’s warmth. Easy to find and a short drive to nearby towns.

This lovely home is in the heart of Lenox. In warmer weather, it is walkable to the shops and restaurants of Lenox, or is a two minute drive. It's well located to discover the best of the Berkshires. The bedrooms were spacious and the family space was cozy, including a large couch for lounging and a lovely eat-in kitchen for meals. Great set up for a family. We loved our stay and are already planning for more visits for summer hiking and more local mountain skiing next winter.

Paul’s house was great! Highly refs if you’re skiing in the area.

Niki and Adam’s place was wonderful! Space for everyone, well equipped, comfortable and clean. Communication responses were quick and clear. All 3 generations of my family thoroughly enjoyed their home and its surroundings. Highly recommend!

Staying at Amanda and Andrew’s place in Canaan, CT is an exceptional airbnb experience. The home and property are in excellent condition, exactly as pictured in the airbnb profile . And, Amanda and Andrew are quintessential hosts, friendly and responsive. We cannot recommend staying here highly enough. Thank you Amanda & Andrew !

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!

My partner and I (and our pups) loved our stay at Mian and Anthony’s home! The home was in a perfect location for what we needed, clean and comfortable, and overall great vibe. ✨ Hosts were super friendly and helpful. We would definitely stay again next time we’re in town!

Absolutely fantastic stay! (this is our third time staying here) Rob and Julia are excellent hosts—welcoming, responsive, and incredibly flexible. The house is impeccably maintained, clean, and looks great. We loved our walks and runs around Sherwood Forest and swimming in the lake. This is our third time staying here, and we can’t wait to return!

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.

The house was a happy place to spend holidays with family. Our two-year-old loved the play kitchen next to the real kitchen and we loved the great room with the gas fire place. The house was tastefully and lightly decorated for Christmas, which we appreciated coming from afar, and there were enough pots and pans to, as the host said, prepare a feast. We wished we had known the basement was not heated, though perhaps we missed that, but we made use of that fun space anyway with the help of warm sweaters. We would rent again!

We enjoyed our stay with our family. Great places to hang out and eat together. Also liked the quiet spots for reading.

Lovely cabin in a secluded location, perfect for a quiet romantic getaway. We loved how homey and modern it felt, close to town center and grocery stores, yet very peaceful and picturesque. Amazing duvet comforter that now has us searching for one just like it! Thanks for everything!

Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

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

We had such a lovely stay at John and Amanda's gorgeous home. The setting was incredibly peaceful- and the home has been so beautifully restored. The interior is impeccably designed and stylish, oozing with charm while also offering all the modern amenities you'd seek while on holiday. John and Amanda responded promptly to any and all questions and made everything so easy from the onset! Our two kids especially loved the reading nook:) We look forward to booking again in the future!

Kelsey’s place was nothing short of perfect. My family and I hadn’t been back to Mass in many years, and we needed a good place to have everyone together again in one place - this place fit the bill and more! The house and backyard are beautiful. You get plenty of space while still feeling cozy. The backyard was perfect for a BBQ and the grass area provided plenty of space for my kiddo to run around and play. You’re also wicked close to the lake and have plenty of places to explore. Kelsey was extremely responsive and kind, and even let us extend our stay a few days because we were having such a wonderful time. I hope to stay here again when we come back next year!

This was our second stay after the first a year ago. So we knew what to expect and were not disappointed. This sweet place and location are perfect for a Berkeshire vacation combining hiking with the amenities of Great Barrington.

I was looking for a month-long stay in the Berkshires, and the barn was the perfect home away from home! It is such a uniquely charming space in a beautiful, peaceful area (even with train tracks close by, they were not very frequent). Abigail was always super responsive and helpful when I had questions and very friendly; I wish all hosts were like her! She also has the best recommendations for restaurants and things to do. Her, and the property manager, Robinson, were both quick to act if I had an issue, and they’re both so nice! I would definitely stay here again. Thank you for everything, Abigail!

We enjoyed our stay at Elijah’s place. It was just as described and Elijah was very responsive before and during our stay.

We had a wonderful stay at this cozy and beautiful cabin! It was exactly the quiet, relaxing, and secluded getaway we were looking for. We were welcomed with a beautiful basket full of goodies. The bed was comfortable, and the sauna and large jacuzzi tub were perfect for unwinding. The kitchen was well-equipped, and having both a crock pot and air fryer made meal prep super convenient. We really enjoyed the cozy wood-burning fireplace. Communication with Elle was excellent—she was very responsive and helpful throughout. Although it rained during our visit and we didn’t get to use the outdoor spaces much, there are some lovely spots for enjoying a fire or just relaxing outside.Highly recommend this cabin for anyone looking to recharge in a peaceful retreat!

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

Bradley’s place is hands down the best spot I’ve stayed at! It had everything I needed— a jacuzzi, an outdoor fireplace, and a spacious, clean bathroom& yah - perfect wine glasses! The entire space was spotless and well-maintained, offering both comfort and privacy. The host was incredibly friendly and welcoming, making the stay even better. The area is peaceful and quiet, perfect for a great night’s sleep and a fresh breath of air. If you’re looking for a relaxing getaway, this is the place to be. Wine, snacks, small items available, lots of towels, washer and drying available! Pet friendly - my dog Mark enjoyed the free and safe space! Scenic areas, accessible - and yah - Amazing places to eat around- His recommendations - hit the right spot! Highly recommend supporting this business! Thank you for everything Bradley! We will always be back and your place will always be no 1- best get away from home!

Gillian was a super host. The place was clean and ready for us when we arrived including a decorated Christmas tree, doggie dishes, and a full wood pile. She got back to us in a timely manner for all questions. And all expectations and facts about our stay were communicated in a clear way. Thank you Gillian!

This is a very beautiful Berkshire property that is also very conveniently located. The 2 bedroom barn is spectacular and is where we 5 spent all of our waking time. The farmhouse is where the rest of us slept (3bedrooms). We used the fully equipped kitchen in the barn. We didn’t spend our together time in the house as it isn’t as open, light, contemporary or spacious as the barn. The house does have smaller dens/living rooms to accommodate groups bigger than than the 5 of us. Both the Barn and the house have gorgeous backyard panoramic Berkshire views - one with a patio and the other with a deck. Perfect place for us (5 older women) and a perfect place for multi family and/or multigenerational clan to enjoy time together This is a great Berkshire location with lovely hosts!