Archaeological site mapping is important for both understanding the history as well as protecting them from excavation during the developmental activities. As archaeological sites generally spread over a large area, use of high spatial resolution remote sensing imagery is becoming increasingly applicable in the world. The main objective of this study was to map the land cover of the Itanos area of Crete and of its changes, with specific focus on the detection of the landscape’s archaeological features. Six satellite images were acquired from the Pleiades and WorldView-2 satellites over a period of 3 years. In addition, digital photography of two known archaeological sites was used for validation. An Object Based Image Analysis (OBIA) classification was subsequently developed using the five acquired satellite images. Two rule-sets were created, one using the standard four bands which both satellites have and another for the two WorldView-2 images their four extra bands included. Validation of the thematic maps produced from the classification scenarios confirmed a difference in accuracy amongst the five images. Comparing the results of a 4-band rule-set versus the 8-band showed a slight increase in classification accuracy using extra bands. The resultant classifications showed a good level of accuracy exceeding 70%. Yet, separating the archaeological sites from the open spaces with little or no vegetation proved challenging. This was mainly due to the high spectral similarity between rocks and the archaeological ruins. The satellite data spatial resolution allowed for the accuracy in defining larger archaeological sites, but still was a difficulty in distinguishing smaller areas of interest. The digital photography data provided a very good 3D representation for the archaeological sites, assisting as well in validating the satellite-derived classification maps. All in all, our study provided further evidence that use of high resolution imagery may allow for archaeological sites to be located, but only where they are of a suitable size archaeological features.