This article looks at Ashkenazi-operated hotels in Tiberias, Beirut, Jerusalem, Jaffa, Cairo, Alexandria, and elsewhere, in the late Ottoman period and under British rule, to consider the confusing ambiguities that these stories reveal. Ashkenazi presence in Palestine is typically understood in terms of either the pious, zealot pilgrims, or the nationalist settlers. And yet the story of the hotel owners and operators could also fit into a different category, that of migrants, who sought to integrate within existing social, economic, and political structures. The tourism and hospitality industry, which relied on flows of people across borders and on a diverse customer-base, was to some degree at odds with the segregation associated with Zionist Yishuv. Such stories, which have been forgotten and erased by the history of Palestine in the twentieth century, prompt us to rethink our understanding of Ashkenazi history in the region.