: In high-altitude alpine regions, water within fractured rock masses undergoes a water-ice phase transition under subzero temperatures. The resulting frost heaving pressure can easily induce stress concentration at the tips of existing fractures, leading to the initiation of new microcracks and ultimately causing damage and deterioration of the rock mass. This study employs a monitoring system composed of thin-film sensors, temperature sensors, and a strain gauge to investigate the influence of freezing temperature, fracture size, and inclination angle on the frost damage characteristics of rock masses by monitoring the temperature, frost heaving pressure, and deformation at fracture tips during freeze-thaw cycles. The experimental results indicate that: (1) The evolution of frost heaving pressure in water-saturated fractured rock masses sequentially undergoes five stages: incubation, rapid increase, relaxation, secondary growth, and dissipation, while the evolution of frost heaving strain includes five stages: thermal contraction, rapid increase, slow increase to stability, secondary increase, and thawing contraction to residual strain stabilization. (2) After freezing, the fracture ice is significantly extruded, and frost heaving cracks form at the fracture tips. (3) The first and secondary peak frost heaving pressures increase linearly with decreasing freezing temperature, grow exponentially with increasing fracture width, and decrease gradually with increasing fracture inclination angle. (4) Analysis of the frost deterioration mechanism shows that during the freezing process, when the ice plug reaches a completely sealed state and no longer slips, the frost heaving pressure and strain inside the fracture rise sharply to their peak values, causing stress concentration at the fracture tips and generating microcracks. During the initial thawing stage, a secondary increase in frost heaving pressure occurs inside the fracture, further exacerbating rock damage. The findings of this study can provide a reference for gaining deeper insights into the initiation and evolution mechanisms of frost heaving pressure in fractures, as well as for conducting numerical simulations and theoretical analyses of frost heaving propagation.