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In southwestern Massachusetts, between the village of Ashley Falls and Great Barrington, Sheffield sits in the lower Berkshires full of vibrancy and adventure. Sheffield vacation homes and vacation condos are lovely accommodations, overlooking the grassy fields and forested sloping hills that make up the geography of this area. Sheffield is the oldest town in the Berkshires area, and the history that has been preserved is evident. Visitors come from all over to visit the Colonel John Ashley House, which was built in 1735 and is the oldest existing home in the Berkshires. Still a strong agricultural community, Sheffield claims many dairy and poultry farms. Your Sheffield vacation home or vacation cabin will be just minutes from Connecticut to the south and short drives to northern Berkshire communities.