Pet-friendly holiday 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.

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

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!

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!

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

This Airbnb exceeded our expectations! The house is spacious and super family friendly (also great for just adults). We loved the Airbnb so much that we only left the house once. Our hosts were very attentive and accommodating. I would recommend to anyone who is looking for a getaway in the Berkshires no matter the season.

We had a great time - coming from the city, it was a perfect rural getaway for us. It was also a short drive to downtown Lenox. Thank you for a lovely stay!

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 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!

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

I have nothing but wonderful things to say about Teva and his lovely home. The house is spacious, tidy, comfortable, and the surroundings are beautiful and peaceful. The beds were comfortable and everything you would need is there. We skied at Catamount which was ~20 minutes away - super convenient. Finally, and most notable, the overall experience and Teva’s attention to his guests’ experience was outstanding. He promptly and proactively reached out with local recommendations, was accessible during our stay for any questions, and made us feel right at home. We hope to come back over the summer for a little getaway.

House was absolutely adorable. Cozy and warm. Felt like we were in the middle of nowhere, but we were close to everything - would certainly stay again.

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!

This is a special home with loads of history. I arrived to a snow covered wonderland. By the time I left a few days later, purple flowers bloomed and birds chirped under the Spring sky. The home is quiet, light-filled, comfortable, and inviting. I only used the main floor, aside from taking advantage of the laundry area. I spent most of my time on the back deck off of the bedroom. Coffee, watching the sun rise and set, stargazing, listening to the water... I had zero interest in tuning out the sounds of nature. My dog and I walked the large property much of the day. It is secluded yet a short drive to most. Lisa is a kind, accessible, and flexible host. This is the place to stay for a city detox, and I hope to return in another season!

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!

We had a wonderful weekend staying at this property. It was exactly as pictured, perfectly clean, very well appointed, and excellent communication from the host. Great spot for a peaceful weekend in the Berkshires & Great Barrington! Would definitely book again. 🙏✨💖

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!

Carmen's apartment is clean, well-stocked and is exactly as described on the website. It's 5 minute drive from Tanglewood and Lenox. Carmen responded immediately when contacted and was very helpful.

This place is an absolute gem. Definitely one of our favorite Airbnb‘s we’ve ever had the privilege of visiting. The setting is spectacular, and the house is so charming and well equipped. Our kids had a blast and we definitely enjoyed the Jacuzzi in the master bathroom. It’s easy to tell that this is a treasured family cabin, lovingly tended to. Very accessible to Great Barrington and loads of wonderful hikes nearby. I highly recommend!