The identification of persistent radio sources (PRSs) coincident with two repeating fast radio bursts (FRBs) supports FRB theories requiring a compact central engine. However, deep non-detections in other cases highlight the diversity of repeating FRBs and their local environments. Here, we perform a systematic search for radio sources towards 37 CHIME/FRB repeaters using their arcminute localizations and a combination of archival surveys and targeted observations. Through multi-wavelength analysis of individual radio sources, we identify two (20181030A-S1 and 20190417A-S1) for which we disfavor an origin of either star formation or an active galactic nucleus in their host galaxies and thus consider them candidate PRSs. We do not find any associated PRSs for the majority of the repeating FRBs in our sample. For 8 FRB fields with Very Large Array imaging, we provide deep limits on the presence of PRSs that are 2--4 orders of magnitude fainter than the PRS associated with FRB\,20121102A. Using Very Large Array Sky Survey imaging of all 37 fields, we constrain the rate of luminous (10 erg s) PRSs associated with repeating FRBs to be low. Within the context of FRB-PRS models, we find that 20181030A-S1 and 20190417A-S1 can be reasonably explained within the context of magnetar, hypernebulae, gamma-ray burst afterglow, or supernova ejecta models -- although we note that both sources follow the radio luminosity versus rotation measure relationship predicted in the nebula model framework. Future observations will be required to both further characterize and confirm the association of these PRS candidates with the FRBs.