Pet-friendly holiday rentals in Great Barrington

We had a wonderful time at Michelle’s place. The house is spacious and full of charm, nestled in lush greenery that made the stay even more relaxing. Michelle was incredibly friendly and responsive, and we felt right at home.

We had a great stay at Shiyrah’s home! We were a group of 2 families with three little ones with us. The house was perfect for us. Shiyrah was so accommodating, allowing us to check in early with all the kids, as we were arriving for a wedding weekend event a bit before the typical check-in time. She even messaged me the morning of our check-out saying to take our time and not to rush. She is a wonderful and thoughtful host, and her house is a beautiful place to stay. Thank you so much, Shiyrah!

Jaryn’s home was wonderful, the outdoor space really make this home , we were truly able to relax. It is also in a really convenient location. Thanks for a wonderful stay.

Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Beautiful area and beautiful house – well-designed, spotless, and equipped with everything we needed. It looked even better in person than in the photos. The open family area was amazing and spacious. We also had a lot of fun exploring the farm and surrounding property. Definitely one of the loveliest Airbnbs we've stayed at. Highly recommend!

We stayed here for the weekend of our son’s graduation nearby, and it was the perfect place to land. The house is beautiful and full of charm, with original artwork, comfy chairs, and inviting spaces to gather and relax. You can really feel the care and attention the hosts put into making it special. Thanks to a stretch of spring rain in the area, the landscape around the stone house was vividly green, lush, quiet, and full of life. One of our favorite moments was sitting on the bed and being surprised by a hummingbird visiting our window. Such a lovely and memorable stay!

The airbnb was close to town. The house was very clean and comfortable.

My friends and I spent the long weekend here for my bachelorette, we definitely could not have found a better place! Each room has been decorate with such style and care, everyone was blown away that it was even cuter in person. There was plenty of space for everyone to be comfortable, and the two living spaces were perfect for us to hang out and play games. We were also able to put to use the included kayaks as well at the hot tub, which was perfect for the unexpectedly chilly end to our weekend. Vincent’s instructions were super clear and communicated ahead of time, not to mention, it felt like all of our needs were anticipated with included toiletries and kitchen/bar supplies. The stay was seamless start to finished. We definitely hope to stay here again!

Robert was an excellent host. Proactively reached out with help to find the home, and a whole host of recommendations. Great space, very private, and had everything you could need.

Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Had a beautiful stay and would 100% return and tell friends about it. Cute and cozy stay, lovely little town and beautiful views.

Really clean and well thought out B&B. Very quit surroundings. Would gladly stay again.

A lovely break from the city - which is exactly what we wanted. Our dog loved it too. The barn is spacious and well appointed and the grounds are perfectly maintained.

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.

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!

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

What a wonderful treat it was to stay at Andrew and Suzanne’s! The space is incredibly comfortable and feels very homey. The place gives the feeling as if you’re staying with family but with all the pampered touches of a hotel. Great location to base yourself from if you want to jet set around the Berkshires!

This was a great weekend getaway for two of us. The apartment is pristine and private. It was a great base camp for outings in the Berkshires. Stockbridge is just one mile away up the road and has tons of cute shops and restaurants.

Timothy’s place is so relaxing. His place was perfect for our group of 8. Plenty of space for all. Timothy was very responsive when we reached out with a question. The location was perfect. It was very peaceful sitting out on the porch listening to the birds. This place is in walking distance to the Appalachian Trail. We will definitely be booking again.