Herein, we report a rare example of rhodium-catalyzed C-H activation/[4 + 2] annulation of alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity of the rhodium catalyst in this study differed from that observed in cobalt-catalyzed C-H activation/[3 + 2] annulation between vinylic amides and bicyclic alkenes. In addition, the reaction was performed in EtOH at room temperature, which also displayed excellent diastereoselectivity, good functional group tolerance, and air compatibility. A series of novel bridged-ring skeletons were obtained in good to excellent yields. Scale-up experiments were carried out with 1 or 0.75 mol % rhodium catalyst, affording the desired bridged-ring skeleton in excellent yields.