Search Vacation Homes in Sheffield

"Place looked great in pictures and turned out to be even better! Will definitely stay there again."

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "

"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"

"Our family had a wonderful experience and stay. "

"Home was very nice and as described. Perfect for our needs "

"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."

"Our family had a wonderful stay at the beautiful, clean, peaceful Hoyt House. There was plenty of space to gather together as well as spread out. The daffodils were beginning to bloom and there is the sight and sound of a running stream behind the home. We were close to fun things to explore like the Audubon, covered bridge, and Kent waterfalls. Great bakery, restaurants, grocery a short drive away. The heated indoor swimming pool was the biggest hit. We hope to have the opportunity to...

"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."

"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...

"Proximity to Catamount was ideal. Short drive to Great Barrington. The place was nice and sunny, and very comfortable. The mud room was fantastic for stowing gear and dressing in ski clothes. Overall, a very nice property. "