In this study, different amounts (from 2% to 4.5%) of dietary fiber-rich cranberry pomace (CP) were added to yogurt before or after fermentation to increase dietary fiber content without changing the textural properties of the product. The addition of CP reduced whey loss, improved the firmness and viscosity, increased the total phenol compound content and the antioxidant capacity values (DPPH center dot, ABTS, and ORAC) of the yogurt in a dose-dependent manner, and had no significant effect on the viability of the yogurt culture bacteria. For all CP-supplemented yogurt samples, the bioaccessibility index of the polyphenols after in vitro intestinal phase digestion was approximately 90%. However, yogurt with CP added before fermentation exhibited a significantly (p < 0.05) lower degree of protein hydrolysis post-gastric and post-intestinal than the yogurt with CP added after fermentation. Yogurt supplemented with 4.5% CP could be considered a good antioxidant dairy product and a good source of dietary fiber.