Existing research on historic hotels has identified their role as key projections of community ideals and place identities, as ‘hip’/creative business ventures and as dark tourism sites of ‘darkness', difficulties and dissonances. However, there has been less discussion on what happens when these intentions and operations come together in a single historic hotel. Specifically, we argue that the historical Lloyd Hotel in Amsterdam was recently adapted to function as a ‘quasi-freedom machine’ for cultural and heritage guests and visitors – a building to be unchained materially from its carceral pasts via extensive conservation and to become a liberating space for cultural, heritage and hospitality users. Drawing on the narratives proposed by the architects and managers adapting the building and the accounts of its former (juvenile detention centre worker) and current users (hotel guests and cultural tourists), this paper examines the convergences and divergences related to the creation of such a single ‘utopian’ space, also in relation to its painful past and cultural touristic present. In doing so, the article intends to contribute to the understanding of the relationship between utopian (liberating) visions of and user practices in historic hotels marked by difficult histories.