A label winding device is for receiving a medium including a label liner and a label member that is removably attached to the label liner and has at least one label portion and a waste portion, separating the waste portion from the label liner at a waste separation portion, and winding the at least one label portion with the label liner. The label winding device includes: a waste winder for winding the separated waste portion; a label winder for winding the at least one label portion with the label liner without the separated waste portion; a waste guide for guiding the separated waste portion to the waste winder; a support for rotatably supporting the waste guide; a sensor for detecting a rotational speed of the waste guide; and a waste break detector for detecting break of the waste portion on a basis of the detection by the sensor.