Before the 2013 season, Berry entered spring training in competition for a spot on the Tigers 25-man roster. On March 27, he was optioned to the Toledo Mud Hens, the Tigers Triple-A minor league affiliate. Berry hit .323 (10-for-31) with seven RBIs, three walks and six strikeouts in Grapefruit League play, but had also missed some time due to patellar tendinitis.
Berry began the 2013 season playing for the Toledo Mud Hens. However, Berry was designated for assignment when Detroit traded for Francisco Martínez to make room for Martínez on the 40 man roster. Berry was designated for assignment on June 2, 2013.
On August 27, 2013, Berry was traded to the Boston Red Sox for Clayton Mortensen. He appeared in only 13 regular season games for the Red Sox, but hit .625 with a home run, 4 runs batted in and 3 stolen bases, earning him a postseason roster spot for his base-stealing abilities. Berry did not have a plate appearance in the 2013 postseason, but made three pinch-running appearances and went 3 for 3 in stolen base attempts, earning his first career World Series ring when the Red Sox defeated the St. Louis Cardinals for the title. The Red Sox released Berry on December 23, 2013.