While both The Woman in Black and Winchester are both gothic ghost stories, Winchester‘s lady in black doesn’t succeed as well as The Woman in Black due to trying to hit too many targets. (Sorry not sorry.)
Both films feature a lot of great (and admittedly grey filmography), and both have some star power (through Daniel Radcliffe and Helen Mirren). But you should note that I say that both are gothic ghost stories and not "horror movies", and I make that distinction for a specific reason: Neither is particularly scary, though they’re both creepy and atmospheric.
You can disagree about my definition about "horror movies" (and I think the first comment on my post about the recent film version of IT posits a great rejoinder), but what I mean here is this: neither of these films works very well as a modern "scary" movie. Indeed, I think Winchester‘s downfall is by trying to shoehorn jump scares and a "Hollywood" mentality into a gothic tale.
The emotional heart of both films are twined around the prongs of a wronged ghost seeking (misdirected) justice and the emotional wounds of a widower thrust into the mystery. In true gothic fashion, an emotionally wounded man of intellect is called in to bring sense to an occult mystery; it is only through their emotional redemption that resolution is achieved. This conflict and resolution of science and emotion, the emotional core of both films, works quite well.
Except that unlike The Woman In Black, the film Winchester seems to have had the modern "scary movie" treatment grafted onto it at the last moment. Completely gratuitous jump-scares abound in the first half of the movie, an action-movie resolution robs the emotional resolution of its power, and a cheap pre-credits clip just feels cheap. As a result, those enthralled by the gothic elements (as I am) feel cheated by the "scary movie" treatment, and those coming for the thrills will most likely be underwhelmed by the measured suspense of the gothic sub-genre – and this seems to be borne out by the differing reviews of the films to date.
If you are looking for gothic chills, check out The Woman In Black, and wait to catch Winchester until it’s streaming for free.