We present detections of emission at 250 GHz (1.2 mm) from two high redshift QSOs from the Sloan Digital Sky Survey sample using the bolometer array at the IRAM 30m telescope. The sources are SDSSp 015048.83+004126.2 at z = 3.7, and SDSSp J033829.31+002156.3 at z = 5.0, which is the third highest redshift QSO known, and the highest redshift mm emitting source yet identified. We also present deep radio continuum imaging of these two sources at 1.4 GHz using the Very Large Array. The combination of cm and mm observations indicate that the 250 GHz emission is most likely thermal dust emission, with implied dust masses of 1e8 M_solar. We consider possible dust heating mechanisms, including UV emission from the active nucleus (AGN), and a massive starburst concurrent with the AGN, with implied star formation rates > 1e3 M_solar/year.