Pet-friendly vacation rentals in The Berkshires

Adorable cottage absolutely ideal for unplugging and relaxing

House was great location, very comfortable- Kimberlie was awesome, thanks for your kindness. Lauren N

We had a wonderful weekend at Chloe's cabin! Beautiful view and access the stream. Within easy driving distance of many great spots.

My family, dog and I had an incredible weekend visit! It was our first time to the area and we already want to come back. Consuelo was a fantastic host! Consuelo was so easy to get a hold of for questions and was so friendly. The place was very organized, quaint and gorgeous. Thank you for a fantastic time! :)

Had a wonderful time staying at Kim’s place — cozy, quaint, and did the job for our weekend getaway. It’s clear that she thinks of the little things, and we really felt like we were in someone else’s carefully curated space. A couple things to note: the heat was quite loud (and I’m a light sleeper), so we ended up turning it off at night. Probably less of an issue in the summertime! Similarly, we had the luck of being rained out most of our visit. The lighting in the cabin is a little precarious for those late nights or cloudy days. Lastly, and this may be partially operator error, but the blinds didn’t really offer a ton of privacy and appeared see-through at night. The location itself was peaceful and secluded, but it’s something to keep in mind if you prefer that extra privacy.

Such a cozy space!!! My small family really did enjoy our peaceful stay. I would definitely book again when in the area. I felt such peace and serenity sitting under the stars, in front of the crackling campfire. It was me and the hubby with 2 of our girls ages 10 and 16. They loved the hot tub and s’mores:). Thanks for the stay.

Comfortable stay in a nice area.

We had a wonderful stay at Bear Cottage. The house accommodated our family of four, with each of us in our own private bedroom and sharing two full bathrooms. We especially enjoyed lounging on the front porch, just off main street and an easy walking distance to all the stores in town as well as a nice local hike (Tanbark Loop). We also enjoyed the backyard, which was spacious enough for lawn games and included a nice fireplace.

The cabin was great, especially the coffee! We enjoyed a lot! The view is beautiful in the woods. The hosts respond quickly and accommodating, and provide all amenities as needed. Recommend it if you are looking to stay away from city life and enjoy a cozy cabin.

Esme is a great host! Super responsive and friendly. The cottage is cute and cozy, as described. It's definitely a place to recommend!

Had an absolutely lovely stay at Billy's cabin! We only stayed one night but it was everything we could have hoped for. Being able to take the canoe out on the river was amazing. Even with the road on the other side of the river it was extremely peaceful. We ate out for every meal since town was so close and easy to get to. All we brought with us was some firewood, water, and an air mattress/blankets/pillows. Would definitely stay here again!!

Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

Beautiful modern cabin in an ideal nature setting. Hot tub and sauna were perfect! The night sky was stunning ! Great restaurants, hiking, farms all within 10 minutes. Perfect 2 day get away! Amazing host. Extremely responsive.

Jeff and Sharon were very responsive and provided us with everything we need to have a great time!

John was a very welcoming and kind host :) He gave us a warm introduction when we arrive and great recommendations The house is immaculately clean, beautiful, comfy and overall very comfy All you can think you need is in the house Some deers came to say hi too! It was wonderful We will be back again soon THANK YOU

I loved everything about our stay here! The cottage was extremely lovely and peaceful, with an especially fantastic library! Jessica was very responsive to a question I had about check out times, and all instructions were as clear as the house was clean (very). Highest recommendation!

This was our second stay at the Riverside Blues House and once again Liza did not disappoint! This is a great location, great view and the home is pristine and beautifully decorated. My son lives nearby and when we have a large group visiting the Riverside Blues House is our home away from home. Can't wait to stay there in the warm weather and take advantage of the Ferry!! Thanks Liza!

Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you

Beautiful place and stay! Private, cozy & peaceful, yet close enough to fun places like Hudson and Kingston. Martina was a wonderful host, super responsive with tons of great recommendations. We absolutely loved our stay!

Ruth was such a great host!! She was extremely flexible and reasonable — and the location was beautiful. Me and my group of friends were able to have such a nice time, stress free at Ruth’s Airbnb!

We stayed here right after our wedding in Westchester county as a "mini-moon" for a couple of days and absolutely loved it! It was the perfect place to relax especially on the patio overlooking the water and the hot tub was an added bonus. This is one of the few Airbnbs we have stayed in that we would go back to in a heartbeat. Beautiful!!! Highly recommend :)

We were two people in this wonderful house for four nights, cooking a lot and enjoying the warmth of the fireplace/stove, as well as the bath. On a break from the city and due to drizzly April weather, we wanted to stay put rather than explore the area. The house was very welcoming, cozy, and secluded for this purpose. Other reviews note that Erika's house is a bit remote. Remote was what we were looking for. The house might be relatively far from specific hikes or sights or, say, Kingston, but we felt the house is actually close to NYC if you want a truly tranquil, private place to relax. Since we love to cook it was great to find ample cookware in excellent condition and the outdoor grill was easy to get started. We wanted to escape the internet, but the internet/wifi is certainly fast for work and play. The bedrooms are as seen in the photos and the king bed and large bedroom were perfect. Yes, we would return to Erika's house!

I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.