Pet-friendly vacation 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!

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!

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

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.

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!

My girlfriends and I had an amazing stay! The house is stunningly gorgeous—even more beautiful than the photos. Every detail was thoughtfully designed, creating the perfect setting for a relaxing and fun getaway. The space was spotless, well-equipped, and incredibly comfortable. We truly had a great time and felt right at home. Highly recommend for anyone looking for a stylish and memorable escape!

Place is beautiful and very relaxing. We really enjoyed our stay in the house and the outdoor with the little river was perfect for our young kids

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!

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.

Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!

The house and property were absolutely lovely, clean, and peaceful. We had everything we needed. When there was a big rain storm and the internet had some issues, the hosts responded immediately and reset the modem and offered to call Spectrum. Issue was fixed right away. The pool was perfect temp and so restorative. Would 12/10 recommend staying here.

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!

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.

Only complaint would be the noise from road during the morning commute

Awesome location! Great views! Very cozy and comfortable! 10/10 stay.

Walt's Place was wonderful! Everything was exactly as pictured. Britta was communicative and proactive, providing check-in instructions ahead of our stay and checking in briefly via text to make sure we were all set once we arrived. We would definitely stay here again if in the area!

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.

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!

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.

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.

We really enjoyed our stay and wish we would have had more time. Appreciated how updated, clean, and free of clutter the place felt. It is a very quiet and peaceful street, but still walkable to the main street, and there is so much to do in the area within an easy drive. We would definitely look to stay here again on a future visit.