In shift work disorder (SWD), disturbed sleep acutely impairs employees' recovery, but little attention has been paid to sleep during longer recovery periods. We examined how holidays affect self-estimated sleep length, sleep debt, and recovery in cases of SWD. Twenty-one shift workers with questionnaire-based SWD and nine reference cases without SWD symptoms completed a questionnaire on recovery and sleep need. They also reported sleep length on two separate occasions: during a work period and after ≥ 2 weeks of holidays. Sleep debt was calculated by subtracting sleep length from sleep need. We used parametric tests to compare the groups and the periods. The groups reported shorter sleep on workdays than during holidays (median difference: SWD group 1.7 h, p<0.001; reference group 1.5 h; p<0.05). The SWD group's self-estimated sleep during holidays increased less above the sleep need (median 0.0 h) than the reference group's sleep (1.0 h, p<0.05). In addition, the SWD group reported good recovery from irregular working hours less often (14%) than the reference group (100%, p<0.001). Although holidays were generally associated with longer sleep estimates than workdays, employees with SWD experienced consistently less efficient recovery than those without SWD.