Pet-friendly vacation rentals in Berkshire County

This place really blew me away. Me and my boyfriend of 7 years wanted to have a private get away with our two dogs for our anniversary and Alissa's place was perfect. We're usually home bodies so this well loved cute little cabin was perfect for us. The view of the property was surreal. We dream of owning a place like this! The pond was so beautiful! Though warning to others that hill back up is no fun haha! The inside was cute and cozy feeling. We couldn't get over how beautiful the kitchen was. The touches of graffiti artwork really did it for us as my boyfriend used to do the same art as well. He also recognized the framed drawing in the living room as well. So cool! Talented artists on display. We only used one bedroom which was small but perfect for us. Also our phones had 56 the whole time which was a nice surprise. Not much to do when you have two dogs so we stayed in and picked up food for the most part. Would definitely come again ideally with warmer weather.

Amazing location for a woman's get-together, so much to do in the home no need to leave for entertainment. Jason was so helpful when needed. one of the coolest places to stay.

We had a great stay at Michael’s cabin. His communication was thorough and he was very responsive to any questions we had. The space is comfortable and peaceful. Just a heads up- a lot of the windows don’t have curtains (upstairs bedroom and bathrooms). I imagine the only things that would see you are deer, but the sun definitely woke us up in the morning :) Well stocked kitchen, which was a huge plus! Thanks for sharing your great space with us!

One of the nicest airbnbs I’ve stayed in! There were so many small details that really made us feel at home and the hosts were very responsive. Home was clean and looks better than the photos! Will definitely be coming back.

Kate was so responsive and kind and made us feel very welcome. The house is full of charm and so cozy. We spent our vacation spread out on comfy couches around the big woodstove. The area is beautiful and peaceful, I loved taking my dog for walks down the road and letting him run around the woods in the backyard. Everything was clear and well communicated and we felt right at home. Thank you Kate!

Had an amazing stay! This cabin was absolutely perfect for a weekend getaway. The location is so peaceful and quiet, making it the ideal spot to relax, but still close enough—just 20 minutes!—to great shopping and restaurants when you want to explore. Highly recommend!

We came to Otis with our 3 young children with the plan for them to learn to ski at the nearby ski school/mountain. We had a wonderful time and John and Loren’s house was perfect for us. They are lovely, accessible and accommodating hosts! We had the good luck of a snowy weekend and the cabin and property were just gorgeous. The cabin is simple, but very comfortable and we enjoyed how cozy it felt. Our kids slept well and and had so much fun, so did we!

Katie's place exceeded our expectations! It was nicely decorated and very comfortable- from the couch to the beds to linens. The house was well stocked for a family and the view was lovely!

This house was great for our New Year’s eve getaway with friends! Very quiet and peaceful and Michelle even left snacks for us. A great host, highly recommend!!

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!

Great stay for weekend getaway! Convenient location and lots to do nearby. Would stay again!

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!

The house was large enough to bring our group of 8 together but with enough space to stay private and split up when we wanted. Kitchen was well-stocked and the location was just 15 minutes to either Catamount or Butternut for skiing. Hosts were also very accommodating during our stay. Overall, a great weekend!

This place was perfect , we rented it for our wedding last weekend at Greywacke Meadows for two nights. It was awesome to have such a cute place to get ready in with my bridal party. Everything was clean and exactly like the pictures. We had a great time , highly recommend!

Nice private location, overlooking the river out back. Plenty of wildlife can easily be spotted by the patient observer. The home was very comfortable inside and out. An abundant variety of music and movies were readily available during our stay. We're looking forward to our next stay for more time in this relaxing location.

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.

This Airbnb was absolutely perfect! The space was spotless, beautifully decorated, and exactly as described in the listing. The host was incredibly accommodating and quick to respond to any questions we had, making our stay stress-free. The location was ideal, close to all the attractions we wanted to visit yet quiet and peaceful. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and memorable experience!

What a lovely place! Great hiking nearby Cozy and comfy Jared went above and beyond. We loved it

My family and I spent a few pre-Christmas days at Meredith‘s Airbnb (there were 9 of us). The house was spacious, bright and comfortable—and clean. There were plenty of bedrooms to accommodate us and did not feel cramped. The kitchen had everything a person could possibly want: plentiful dishes, utensils, bowls, pans, glasses, etc. Our inter-communication was timely. We all agreed that this place was the best AirBnB we have ever rented and would not hesitate to rent it again. Meredith and Jason, you truly have a gem of a home!

We had a very lovely stay as part of our ski weekend at Jiminy Peak. The house is very large with multiple sitting areas. The kitchen was great and we enjoyed the hot tub as well. We had some issues with the lock and heat but the host was very communicative and helpful and it didn’t impact our stay too much. House is in a very beautiful and quiet location - was a real winter wonderland.

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 the pleasure of staying at Min Ji's Airbnb over Thanksgiving, and it was a fantastic experience! We were two families with kids, and the house provided plenty of space for everyone. Each family had their own private area upstairs with 2 rooms and a bathroom for each family, and downstairs felt spacious enough to have a more lively area for the kids in the living room/sunroom and a quieter area in the library for those who wanted to unwind. The sunroom was a perfect playroom for the kids, it was nice and sunny during the day with beautiful view on the surrounding nature. They had a little picnic table where they could draw/ do arts and crafts and a play kitchen which was a hit with the little ones. The living room had a nice gas fireplace which made it very cozy. Bedrooms and bathrooms were very comfortable. The kitchen was well-equipped, making it easy to prepare our Thanksgiving dinner. The entire house was well heated, even the sunroom which could have been cold in the winter.

We spent two wonderful weeks in Diana’s property. We were close to anything we needed. Very quiet and safe neighborhood to walk around. Diana is very responsive and gracious host. We can’t wait to come again.