Vacationers generally experience higher health and well-being levels than nonvacationers. It is unclear if and how health and well-being levels of vacationers change prior to vacation and what potential determinants are. Our research questions were: (1) How do health and well-being change before vacation? (2) Which factors (i.e., vacation anticipation, pre-vacation workload, and homeload) are associated with health and well-being changes before vacation? (3) Are associations between pre-vacation work- and home-load and health and well-being changes before vacation different for men and women? In a longitudinal study, 96 Dutch workers reported their health and well-being in the two weeks prior to their winter sports vacation. Health and well-being decreased significantly from two weeks to one week prior to vacation. Anticipation did not affect health and well-being, whereas pre-vacation workload lowered health and well-being. Pre-vacation homeload was also associated with a decline in pre-vacation health and well-being but only for women.