This article uses critical geography and cultural studies theories to examine the conversion of three low-income residential hotels into art hotels: the Embassy Hotel in London, Ontario, and the Cameron House and the Gladstone Hotel, both in Toronto. Situating these establishments in the context of culture-led regeneration, I describe the different stages of economic decline and prosperity in the surrounding districts. I develop current literature by analyzing the social and class inequities underlying art-based rebuilding projects that have driven up property values and displaced the urban poor. I suggest that in all three cases the cultural readaptation of the hotels formed part of commercial development and perpetuated the attendant disparities underlying regeneration schemes. However, the proprietors also supported art collectives that engaged in critical cultural practices by reclaiming public city spaces as sites of discord and dissent. In assessing exhibitions and performances, I examine the conflicts and tensions surrounding creative initiatives that both enfranchised and disenfranchised neighbourhood communities. It is precisely the paradoxical workings of art-led revitalization that define the cultural and political histories of hotel redevelopment projects in downtown cores.