This study aims to estimate the coefficient of price demand elasticity for various lengths of stay and booking horizons (as selected factors) to understand their position in the decision-making process and changes in the customers’ willingness to book in different market situations. The study uses a log–log regression model based on OLS and data mined from a selected hotel in central Prague. In total, 33,199 reservations were used for the analysis. The results show that the leisure market segment tends to be more elastic than the corporate clients. In addition, the demand is elastic only for the leisure segment for 31–60 days before arrival. Significant effect on the estimation is held by the contracted business and reservations made for the longer stays, where the hedonic characteristics of the accommodation facility play a more significant role than the room rate, which the revenue manager might use to increase the overall performance of the hotel and gain a certain level of occupancy. The study proposes further research on customer behaviour, which will address more of the variables and will be based on the empirical hard data. The study’s most significant limit is the use of single-property data and a low level of external validity. On the other hand, the results are quantifying previous paradigms and assumptions.