The aim of this paper is to focus on the different distribution channels used by hotels today and to analyze the strategies hotels implement in order to increase direct bookings. Qualitative research was conducted using semi-structured, in-depth interviews with a convenience sample of 15 hotel managers in Crete, Greece. Crete is a popular destination that was developed based on the mass tourism model, experiencing all the pathologies of this model, including the high dependence on tour operators. The results provide useful insights into how hotels operate and handle their bookings. Although tour operators remain very important for hotel sales in Crete, online travel agents (OTAs) are gaining more and more ground in the distribution of their products. For example, Booking.com seems to be an extremely important sales channel for hotels today. Nevertheless, all participants emphasized that they aim to increase direct sales, and for this reason, they have integrated booking engines into their websites. However, this is not enough to attract customers’ interest. Hotels offer their customers exclusive benefits such as loyalty member discounts, early booking offers, and a lowest price guarantee in order to increase their direct sales. Differences were observed between the hotels that participated in the survey depending on their size and category. The paper concludes with recommendations on how hotels can increase their direct bookings and avoid paying commissions to OTAs and other traditional intermediaries.