An English aristocrat, poet and writer, Lady Mary Wortley Montagu (1689-1762) was a privileged and distinguished woman traveller in her time. During her sojourn in Ottoman Istanbul, she noted down significant details as regards the Constantinople and seraglio through her vivid descriptions as a liberated woman in her Embassy Letters. Another significant oriental work, Letters from Turkey by Kelemen Mikes (1690-1761), who was a Transylvanian-born Hungarian writer and political figure, is centered upon Mikes’s life in exile between the years 1717 and 1758 within the boundaries of the Ottoman Empire. In Letters from Turkey, we can feel his strong sense of Hungarian identity and his steadiness in maintaining his cultural and religious customs and values in his elaboration of his own and the “other” culture, while his praising the benign and merciful ruling style of Ottoman Sultans offers a different view of orientalism in favour of the “other” culture (Ottoman Empire). Therefore, the purpose of this paper is to examine the Letters of Lady Mary Montagu and Kelemen Mikes from their political, ethnical, religious and personal perspectives and trace several relationships that has allusive discussion relativity in the discourse of Orientalism. After having explained the specific letters of both writers, I will attempt to use the scope of Edward Said’s Orientalism and Enlightenment Orientalism discussed in Sirinivas Aravamudan’s Enlightenment Orientalism: Resisting the Rise of the Novel, as a magnifying glass to different oriental images and conceptions contradictory with the reality in the eighteenth century. This study will mostly make use of Edward Said’s account of orientalism as well as Stephen Greenblatt’s theory of Self Fashioning in order to explicate the differences as to how the Orient is perceived by the authors from different cultures but from the same period. In order to highlight how the definition of Orient changes, this paper attempts to define the Orient in accordance with the works of Lady Montagu and Kelemen Mikes.