Digital transformation and technology development in Industry Revolution (IR) 4.0 are here to stay. The automation, digitalization, robotizing, and a tsunami of innovations that make up IR 4.0 are making their presence stronger as days go by. Newer technologies, like AI, Big Data, the Internet of Things (IoT), and machine-based algorithms, have given the world various choices of high-speed connectivity through online bookings, online shopping, chats, blogs, and virtual realities. AI and technologies have infused digital transformation and continued to dramatically alter the hospitality industry. This qualitative paper aims to explore what type of digitalization has been incorporated and the challenges faced aftermath. The interview results from eight hospitality managers reveal that all hotels except one have incorporated newer technologies mildly aligned with IR 4.0 within their hotels. All the hotels face trials related to technology, namely budgets, rapid upgrading of digitalization, and insufficient technical employees to oversee the administration of these systems.