This investigation addresses a pressing anxiety of our time – that of homelessness. Tersely stated, the philosophical significance of homelessness in its more modern context can be understood to emerge with Nietzsche and his discourse on nihilism, which signals the loss of the highest values hitherto. Diverging from Nietzsche, Heidegger interprets homelessness as a symptom of the oblivion of being. The purpose of the present enquiry is to rigorously confront humanity’s state of homelessness, and at the same time illumine the extent to which Heidegger’s thought engages with this pervasive phenomenon. In questioning the nature of homelessness, Heidegger’s preoccupations with nihilism and modern technology prove crucial. Moreover, his attempts to overcome or prepare for the overcoming of this state of homelessness are also of great import to the current investigation. Adorno and Lévinas offer scathing critiques of Heidegger’s thought as it relates to the motifs of homelessness, homecoming (Heimkunft) and the German Heimat, for they associate it with provincialism, paganism, and a pernicious form of politics. In providing these critiques they bring to light the risks involved in undertaking a homecoming venture, and they also show how a great thinker can err greatly. While acknowledging the importance of these criticisms, the present study reveals how Heidegger’s various discourses on homelessness and homecoming bear fruitful insights that can contribute not just to a Germanic sense of homecoming but to a sense of homecoming that humanity at large can relate to and be enriched by.