Bed and Breakfast innkeeping as a form of self-employment is often perceived by aspiring innkeepers as a lifestyle choice that seemingly integrates work and life and enhances personal well-being. On the other hand, innkeeping as a business is known for long work hours and limited escape from work due to the blurred physical and temporal boundaries between work and life. Given the paradox, this exploratory study examined the respite experience (an interval of rest and relief from work) of innkeepers and its effect on subjective well-being. The findings from an online survey among 327 innkeepers in the United States reveal that innkeepers lack short-term respites at regular intervals. Engagement in active and high-effort social or hobby-based respite activities is found to be a primary pathway to an effective respite experience in the absence of psychological detachment from work. The results show that respite experience has a significant effect on an innkeeper’s subjective well-being after controlling for job demands, entrepreneurial motivation, and financial performance of the inn. This research has also identified three clusters of innkeepers (lifestyle innkeepers, seasonal innkeepers, and career innkeepers) based on their respite characteristics and other related operational and individual variables.