Dig around the circumference of the drip line. Cut off as little of the roots as possible. Dig the new hole 1. 5 the width and 2. 0 the depth. Put the plant in. Fill the hole 1/3 and put water up were you filled. Repeat the process until you're done.
Transplanting should be done in early spring or in the fall. Dig around the dripline of the shrub, leaving plenty of soil around the roots. Water well the following year.
It is a two-step manipulation. First this fall you need to prune the roots of the holly bushes, using a spade to section the roots around the bush. Then next spring, you can uproot the bushes with a large enough root ball.
