The vagueness of Astarion sleeping mechanics drives me mad sometimes
So, the game says that elves don't sleep - to the point where it's ironically stated that the only way for them to experience sleeping is to either drink a potion of Angelic Slumber or "get hit really hard with a chair".
Instead, they enter a semi-aware meditative state (Revery) where they experience memories from their past lives (usually most positive and emotional parts). Or they just sorting through their current memories.
Now, we've seen Astarion meditating if his way of lying on a bedroll is anything to go by. He is also immune to sleeping spells. We could also see him sleeping (in a Durge run). I know that devs technically recycle the same sleeping pose for all romanced companions, but still. Also, Astarion has nightmares, which is not typical for elves.
Of course, when I was going through the lore, I scratched the surface, but from what I understood, Revery is supposed to be a controlled state, and nightmares aren't exactly controlled.
But, I've found a very interesting bit that (so far) is still considered part of the official canon:
Elves can sleep and dream just like any human, but almost all surface elves avoid doing so. Dreams, as humans know them, are strange and confusing to elves. Unlike the actual memories of one’s primal soul, present life, or past lives, dreams are uncontrolled products of the subconscious, and perhaps the subconscious minds of those past lives or primal souls as well. An elf who dreams must always wonder whose mind these thoughts first arose from, and why. Priests of Sehanine Moonbow are an exception: they sleep and dream to receive signs from their god, and elves consult such priests to interpret their own dreams."
From: Mordenkainrn's Tome Of Foes, Chapter 2: Elves
And not only does this little bit explain a lot, but it also provides some food for your fic writing purposes.
Now, I'm entering the headcanon territory, so be warned.
Astarion's access to Revery got horribly fucked up after he had been Turned. Not only does he no longer have access to his previous lives since he is technically dead and plucked from the cycle, but he also can't even have his happy or good memories before he became a spawn. Even if they are still there, somewhere in the memory palace, getting to them requires going through the catalog of traumatic and painful memories he acquired after being enslaved by Cazador. It's like running through a burning house trying to rescue your family photo - and the hall gets longer each time. So, entering a trance means confronting the worst memories of his life over and over because there is nothing else there.
Due to this Astarion may resort to sleeping, which elves don't usually do. Elves don't like dreams because dreams are subconscious, and they can't be controlled, which scares them. For Astarion, however, it means there is a chance of him subconsciously dreaming of something nice or just being blissfully empty. However, it doesn't safeguard him from nightmares which (because they are the product of his unconsciousness) get even more twisted than simple memories.
Additionally, there can be a possibility that after becoming a spawn he got cut off from meditation and trances completely, relying on sleeping only: at least, the cut spawn epilogue by Withers mentions how while Astarion needs to sleep again, he doesn't sleep alone. While we don't know what that means exactly (and whether it will ever be implemented in the game), I assume that the tadpole gave him the ability to meditate back, but it was a small improvement because his memory headspace no longer holds happy memories capable of offering solace or refuge.
So, my personal headcanon is that he switches between meditating and sleeping depending on how aware he needs to be, and whatever option feels less torturous at the moment.
For instance, in his Origin run, when he remembers the moment of Cazador carving scars into him, he is in a trance. Which is why the memory is so horribly vivid, as if he is reliving it anew.
However, when he has a nightmare where Cazador finds him, he is sleeping and experiencing a memory affected by his subconsciousness. Which is why he jolts himself awake and desperate to know the limits of his freedom.
So, yes, the man literally can't catch a break.
On a happier note (and for your hurt/comfort fanfiction purposes), once Astarion starts traveling with Tav and the group, his memory bank gets updated with memories that are actually fun and nice, so he has something to linger upon when he is meditating. Sleeping gradually becomes a bit more pleasant experience because his subconsciousness got more material to work with, so the quality of his non-controlled dreams has to gradually improve.
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