Four halogen and hydrogen bonding rotaxane host systems featuring pyridinium bis-amide-iodotriazole/prototriazole and pyridinium bis-amide-iodotriazolium/prototriazolium axle components have been synthesized by CuAAC-mediated mono-stoppering chloride anion templation and post-rotaxanation methylation reactions. In competitive 45 : 45 : 10 CDCl₃–CD₃OD–D₂O aqueous solvent media, the dicationic halogen bonding rotaxane displayed a notable enhanced binding affinity and marked selectivity for Br⁻ over other halides and nitrate and dihydrogen phosphate oxoanions in contrast to an all hydrogen bonding counterpart which is attributed to chelated charge assisted halogen bonding interactions.