Ultra-high-performance concrete (UHPC) has become an attractive cast-in-place repairing material for existing engineering structures. The present study aims to investigate age-dependent high-early-strength UHPC (HESUHPC) material properties (i.e., compressive strength, elastic modulus, flexural strength, and tensile strength) as well as interfacial shear properties of HESUHPC-normal strength concrete (NSC) composites cured at different season temperatures (i.e., summer, autumn, and winter). The typical temperatures were kept for at least seven days in different seasons from weather forecasting to guarantee an approximately consistent curing and testing condition (i.e., temperature and relative humidity) for specimens at different ages. The HESUHPC material properties are tested through standardized testing methods, and the interfacial bond performance is tested through a bi-surface shear testing method. The test results quantify the positive development of HESUHPC material properties at the early age, and the increasing amplitude decreases from summer to winter. Three-day mechanical properties in winter (with the lowest curing temperature) still gain more than 60% of the 28-day mechanical properties, and the impact of season temperatures becomes small at the later age. The HESUHPC shrinkage mainly occurs at the early age, and the final shrinkage value is not significant. The HESUHPC-NSC interface exhibits sound shear performance, the interface in most specimens does not fail, and most interfacial shear strengths are higher than the NSC-NSC composite. The HESUHPC-NSC composites at the shear failure do not exhibit a large relative slip and present a significant brittleness at the failure. The typical failures are characterized by thin-layer NSC debonding near the interface, and NSC pure shear failure. Two load-slip development patterns, and two types of main crack location are identified for the HESUHPC-NSC composites tested in different ages and seasons. In addition, shear capacity of the HESUHPC-NSC composite develops rapidly at the early age, and the increasing amplitude decreases as the season temperature decreases. This study will promote the HESUHPC application in practical engineering as a cast-in-place repairing material subjected to different natural environments.