This chapter explores how the objectives of the nascent holiday resort industry transformed in relation to dynamics of health, pleasure, and social class. It analyses the process of defining holiday as a product by drawing on source material from the different actors in the resort economy, including internal documents of the local corporations, resort publications, travel guides, railway advertising, vacationers’ accounts, and medical literature referring directly to holiday practices. It shows that the emotionally loaded encounter between different social classes at the resort was a core aspect of the shifting practices of holidaymaking from ‘taking the waters’ to commercial amusements, or from health to recreation. In order to comprehend these transformations, the chapter focuses on three watering-places that were among the most popular holiday destinations in Victorian and Edwardian Britain, but which differed in their characteristics: Harrogate—an aristocratic inland spa; Scarborough—a spa and seaside resort with mixed social clientele; and Blackpool—the exemplary working-class seaside town. The chapter concludes by pointing to the impact of the therapeutic rationalization of recreational activities on the resort industry, arguing that the notions of health and pleasure in the history of holidaymaking should not be addressed as opposites, but as interrelated concepts defined and valued within a wider context, namely the relation between leisure, class, gender, scientific expertise, and emotion knowledge.