Commercial lowbush blueberry (Vaccinium angustifolium Ait.) and cranberry (Vaccinium macrocarpon Ait.) crops benefit from the presence of honey bee (Apis mellifera L.) for pollination. Unfortunately, beekeepers are observing negative impacts of pollination services on honey bee colonies. In this study, we investigated three beekeeping management strategies (MS) and measured their impact on honey bee colony health and development. Experimental groups (five colonies/MS) were: A) Control farmland honey producing MS (control MS); B) Blueberry pollination MS (blueberry MS); C) Cranberry pollination MS (cranberry MS) and D) Double pollination MS, blueberry followed by cranberry (double MS). Our goals were to 1) compare floral abundance and attractiveness of foraging areas to honey bees between apiaries using a Geographic Information System, and 2) compare honey bee colony health status and population development between MS during a complete beekeeping season. Our results show significantly lower floral abundance and honey bee attractiveness of foraging areas during cranberry pollination compared to the other environments. The blueberry pollination site seemed to significantly reduce brood population in the colonies who provided those services (blueberry MS and double MS). The cranberry pollination site seemed to significantly reduce colony weight gain (cranberry MS and double MS) and induce a significantly higher winter mortality rate (cranberry MS). We also measured significantly higher levels of Black queen cell virus and Sacbrood virus in the MS providing cranberry pollination (cranberry MS and double MS).