An 89-year-old woman had biliary obstruction due to a periphilar cholangiocarcinoma, which obstructed the ducts of the right anterior segment and right posterior segment and the left hepatic duct. We initially performed endoscopic biliary stenting using plastic stents. After successful biliary drainage, we deployed multiple self-expandable metallic stents (SEMS) using a novel combination of the side-by-side (SBS) and stent-in-stent (SIS) methods. First, the two SEMS were deployed in the right posterior segment and left hepatic ducts using the SBS method. Next, another SEMS was deployed in the right anterior segment duct using the SIS method. During the 8-month follow-up period, we performed re-intervention five times. All treatments were successful, suggesting that this new method may facilitate insertion techniques and re-intervention.