Honestly don't know about starting cuttings, but when I lived in British Columbia (similar climate to yours) our neighbor had a whole row of holly trees, and was constantly pulling up seedlings so it seems they seed themselves pretty easily. Could you find someone with a female tree, (see if they are generous) and check under it in the springtime for seedlings instead?
The other caution with starting from cuttings is that holly has male and female trees, and only the female trees make berries, so if you took a cutting off a male tree you'd get another male tree, with no berries. (assuming the cutting rooted) If you root a cutting from a female tree, and there isn't a male tree within pollen range (by bees or the wind, not sure) you'd still not get berries.
It might also be dependent upon starting at a certain time of year. Some cuttings will root in spring but not in fall, or vice versa.
All that being said, no harm in trying. Some trees root soft (new green) wood, and some root from mature wood cuttings, too.
