Studies suggest that there may be an association between sleep and growth; however, the relationship is not well understood. Changes in biology and external factors such as school schedule heavily impact the sleep of adolescents, during a critical phase for growth. This study assessed the changes in sleep across school days, weekends and school holidays, while also measuring height and weight changes, and self-reported alterations in food intake and physical activity. The impact of morningness-eveningness (M-E) on height change and weight gain was also investigated. In a sample of 63 adolescents (mean age = 13.13, SD = 0.33, 31 males) from two independent schools in South Australia, height and weight were measured weekly for 4 weeks prior to the school holidays and 4 weeks after the school holidays. Participants also completed a Morningness/Eveningness Scale and 7-day sleep, diet and physical activity diaries prior to, during and after the school holidays. Participants at one school had earlier wake times during the weekends than participants attending the other school, leading to a significantly shorter sleep duration on weekends for those participants. Regardless of school, sleep was significantly later and longer during the holidays (p < 0.001) and those with a stronger morning preference fell asleep (F18,36 = 3.4, p = 0.001) and woke (F18,44 = 2.0, p = 0.027) earlier than evening types. Growth rate was lower during the holiday weeks. For those attending the school with limited sleep in opportunities, growth after the holidays was lower for those with greater evening preference, whereas for those at the other school, growth was greater for those with greater evening preference. The increase in average weight from pre- to post-holidays was greater for those attending the school with limited opportunities to sleep longer. Participants reported greater food intake during the holidays compared to school days and greater physical activity levels on weekends compared to school days, and school days compared to holidays. Results suggest that time of day preference may impact growth, with evening types who cannot sleep in growing at a slower rate than evening types who can or morning types. This may be related to sleep restriction. Despite sleep being both later and longer during the school holidays, participants' growth slowed during the holiday period. It is possible that this may be a reflection of other behavioural changes in the holidays (increased food intake and reduced physical activity), as sleep timing during the school period was related to growth.