Business and leisure travelers are the two major market segments of the contemporary hotel industry. Besides having different travel motivations, the segments are shown to exhibit differences regarding information search behavior (Jones & Chen, 2011), hotel selection criteria (Yavas & Babakus, 2005), and preferences for hotel attributes (Kashyap & Bojanic, 2000). These facets are well-established research topics represented by a large body of empirical evidence in the literature. Nevertheless, little attention has been paid to the observed differences in reported levels of post-purchase satisfaction between the two segments. It has been shown that for-business hotel service encounters are, on average, evaluated less favorably than for-leisure encounters, with the difference being substantial in its magnitude and robust to controls for numerous relevant factors (Banerjee & Chua, 2016; Lawrence & Perrigot, 2015; Lewis, 1984; Radojevic, Stanisic, & Stanic, 2017). The rare explanations for this phenomenon offered in the literature focus on the personal characteristics of frequent business travelers (Lawrence & Perrigot, 2015) as well as the inconveniences typically associated with business travel (Radojevic et al., 2017), but no conclusive empirical evidence that would support these explanations has been provided. The aim of this study is, thus, to examine in more detail the effect of traveling for business on the evaluation of hotel services. The study employs a multilevel modeling framework to derive an unbiased estimate of the average difference in the reported levels of satisfaction between the two types of encounter, as well as to examine whether the difference changes as a function of certain contextual factors (personal characteristics of the customer, hotel attributes, etc.). The results obtained in this study are important for advancing the existing theoretical approaches to customer satisfaction, especially the dispositional (Plog, 2002; Sirgy, 2010, p. 246) and the encounter (NOE, Uysal, & Magnini, 2010) approaches, but are also valuable to hotel managers, who can learn what can be done to counteract the negative effect of business travel and achieve higher levels of customer satisfaction, which is vital in the highly competitive hotel market.