Pet-friendly holiday rentals in Sheffield

The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!

Such a fun old home, reminded my wife of the old farmhouse she grew up in. The location was perfect for our needs and there was enough space for everyone.

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

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

We enjoyed our stay at Kevin's place. As many others have said, the surroundings are even more beautiful in person. There is another rental unit right across the yard, which we didn't realize, but ultimately we found it nice knowing there were other people around. The kitchen and bathroom(s) were notably gorgeous and comfortable - though we didn't cook, I've never seen a better stocked kitchen in terms of cooking tools at an Airbnb. A spacious and peaceful retreat.

This house was perfect for us (5 friends gathering to fish the Housatonic). Simple, clean, ac/heat/wood-burning stove, all the amenities, and a great hot shower! We were up and down the short path to the river the whole weekend. Amy was a super-host. Attentive when we needed her, but not intrusive. Thanks Amy, we enjoyed our stay!

We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

Madeline is a true professional as a host. This was our third time returning to her place because it has been a great experience every time in all ways. She is responsive and clear about what she offers and what she expects. Strongly recommend her and her beautiful place with great views

The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

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.

Great stay at Jasmine’s well furnished, rustic feel cottage. Peaceful location but just a quick ride to Woodstock, Kingston and Rhinebeck. Pool was perfect - we used it everyday. Heat bathroom floors is a nice touch!

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.

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

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!

We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!

Nice place. Great layout. Easy to navigate. Host was very communicative. We would stay there again.

The home was exactly the way it is in the photos, only better! Everything was clean and spotless. Plenty of kitchen and laundry supplies to use. The home is in a very secluded and in a quiet neighborhood. You will never see another person unless you drive out of the very long driveway and into town. The backyard was scenic and perfect for the fall season. Overlooking the river, especially in the fall is very scenic and was perfect for what we were hoping for. Communication with the Rental property was kind, courteous and professional. The even offered us a late check out as long as they did not rent the property that day. Me and my 5 family members were very comfortable and enjoyed our stay. I highly recommend this property for all seasons. Will definitely return.

We really enjoyed our stay at Jake’s house. He was very communicative and helpful with anything we needed. The house was well cared for and thoughtfully decorated. Our family of 6 was very comfortable and very much enjoyed our stay.

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 !

Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!

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!