To provide a winding device, a winding method and a label sticking device using this capable of easily removing out a wound roll while preventing winding breaking.

The label sticking device 10 is provided with a support means 11 for payably supporting a band-like rolled web R in which a label L is temporarily attached to a peeling off sheet RL; a peeling off means 12 for peeling off the label L from the peeling off sheet RL; a pressing means 13 for sticking the label L to an object W to be attached; a paying out means 14 for giving paying out force to the rolled web R; and the winding device 15 for winding the peeling off sheet RL. The winding device 15 includes a plurality of winding members 37 positioned around a central shaft 30 rotated through a motor M2, and the winding members 37 have one end made to a fixed end and the other end made to a free end. The other end provided leavably/approachably relative to the central shaft.