Understanding the heat transfer of winglet tips is crucial for their applications in high-pressure turbines. The current paper investigates the heat transfer performance of three different winglet-cavity tips in a transonic turbine cascade at a tip gap of 2.1% chord. A cavity tip is studied as the baseline case. The cascade operates at engine representative conditions of an exit Mach number of 1.2 and an exit Reynolds number of 1.7 × 106. Transient infrared thermography technique was used to obtain the tip distributions of heat transfer coefficient for different tips in the experiment. The CFD results were validated with the measured tip heat transfer coefficients, and then used to explain the flow physics related to heat transfer. It is found that on the pressure side winglet, the flow reattaches on the top winglet surface and results in high heat transfer coefficient. On the suction side winglet, the heat transfer coefficient is low near the blade leading edge but is higher from the midchord to the trailing edge. The suction side winglet pushes the tip leakage vortex further away from the blade suction surface and reduces the heat transfer coefficient from 85% to 96% span on the blade suction surface. However, the heat transfer coefficient is higher for the winglet tips from 96% span to the tip. This is because the tip leakage vortex attaches on the side surface of the suction side winglet and results in quite high heat transfer coefficient on the front protrusive part of the winglet. The effects of relative endwall motion between the blade tip and the casing were investigated by CFD method. The endwall motion has a significant effect on the flow physics within the tip gap and near-tip region in the blade passage, thus affects the heat transfer coefficient distributions. With relative endwall motion, a scraping vortex forms inside the tip gap and near the casing, and the cavity vortex gets closer to the pressure side squealer/winglet. The tip leakage vortex in the blade passage becomes closer to the blade suction surface, resulting in an increase of the heat transfer coefficient.