Start evergreen holly bush varieties in February or March and deciduous hollies in either spring or fall. Find this information on the holly bush plant's markers when purchasing or ask about it at a garden center.
Plant holly bushes in locations with full sun, well-draining soil and the required space for the fully-grown size expected. Space the holly shrubs far enough apart and according to the width anticipated when planting several in a row.
Dig a hole double the size of the container or root ball, but the same depth. Virginia Cooperative Extension suggests sloping the sides of the planting hole to make it wider across the top, and then roughing up the sides.
Remove the holly bush carefully from the container. Inspect the roots and cut away any damaged or frail roots. Make several vertical cuts from top to bottom, if the roots are root bound.
Place the holly shrub in the planting hole, and backfill the hole partially. Saturate with water to firm the soil, then finish filling the hole and saturate with water again.
Add a 2- to 3-inch layer of mulch around the base of the holly bush, but keep the mulch away from the stem of the holly plant.
Water the holly bushes weekly throughout the growing season whenever rainfall is less than 1 inch per week. Only water the hollies in the winter season during any long dry periods.