Propagating holly should be done while the bush is dormant. If your holly is deciduous, this means your cuttings won’t have any leaves on them. Although they have no leaves, you will see bumps on the canes. These are known as bud unions. This is where the following year’s leaves are going to grow from. For evergreen hollies, you will take cuttings when the weather is cold and you should remove all but the top two sets of leaves from the cuttings. The bud union on evergreen hollies will be where the leaves meet the stem. Cut at the bottom just below one of the bud unions. Then, from this piece you will partially cut about three quarters of an inch above another bud union, which should give you a good 6 inches of cutting that can be planted. Holly cuttings is not at all difficult. You will simply take your cuttings and dip them in a rooting Compound.

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I took some thelast couple of years fron Ilex aquifoliumthecommon native holly,
I did semi ripe cuttings some tip cuttings too,
look at thebranch, the end is very soft, a littlefurther down its firmer but stillgreen not woody, snip below theleaf joint and remove the leaves
count 3 pairs of leaves up and snip again ......you can remove anothe pair of bottom leaves if nessesary,
pop straight around the edge of a prepared pot.....gritty composts good
continue to fill pot in the same way
if you have lots of plant material do more, I guess I got 3 good ones.

leave them in a ligh frost free place in the shade until next year keep them moist not wet especiall over the winter
when they'll either be showing signs of growth......brown ones are dead ?

i grew some from fresh red berries too.....soil as above but they need a frost so somewhere cold ( even the fridge!)
have fun......lots of shrubs are easier than holly.....euonymus and hydrangea come to mind.....

Many thanks for your very helpful and informative answers to my question Triffedkiller and Pamg. I will put your words into action this Autumn and take the plunge and hopefully succeed with striking and rooting some holly cuttings. I have just tried my hand at taking four hydrangea cuttings Pamg, never done it before just hope I am successful. ?

Its always worth having a go, especially this time of year, I keep mine in a shady part of the gh

there are lots of different ways of propagating plants, maybe worth you looking for a book, possibly in th library.....its such fun growing plants for free.....good luck