In recent years, Vaccinium spp. (bilberry-VMT, lingonberry-VVIT, and blueberry-VCS) have sparked particular interest for their prospective health benefits. The latest investigations have place them as important alternative sources of nutraceuticals as their leaves are the main by-products of berry harvesting. The present study is aimed at investigating the bioaccessibility of phenolic compounds from leaves of the Vaccinium species, both as microencapsulated powder and aqueous extracts, following exposure to in vitro simulated digestion. Moreover, the impact of maltodextrin and glucose microencapsulation carriers on the extracts’ phenolic content was assessed. Prior to encapsulation, the viscosity of the emulsions was shown at a shear stress of 50 s−1 dilatant and a Newtonian behaviour above this value with a final viscosity between 1.024 and 1.049 mPa·s. The final microencapsulation yield for the samples ranged between 79 and 81%. Although the microencapsulated forms presented a targeted release at the intestinal level, the phenolic content decreased after gastrointestinal digestion. The bioaccessibility of the microencapsulated extracts showed higher values than their non-encapsulated counterparts, with the highest value of 45.43% in the VVIT sample, followed by VCS with 41.07%. However, the non-encapsulated VCS sample presented high bioaccessibility after in vitro digestion (38.65%). As concluded, further in vivo research should be conducted on the leaves of the Vaccinium species.