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The other day I read the word どれだけ which means how long; how much; to what extent. I've read several example sentences, and I that's all well and good, but I cannot shake the feeling that it's really counter-intuitive to me.

If どれ　means which; whichever; any and だけ means only; just, I would guess combining them would give some sort of exclusive amount, for example in "Only this many people may enter" or something along those lines.

I may be reading too much into this (or it's gone way over my head), but it still seems strange to me. Are there other question words that have だけ in them? I did a cursory trail-and-error search, and couldn't find any.

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The quick answer: rather than interpreting this as だけ "only", this is 丈 ("length"). Normally read as take, voices during compounding.

Before someone calls me out on it, the more precise answer: both are the same word. The word dake "only" is written as 丈 and derives from 丈 (take). The translation "only" is not always appropriate as is clear in this case.

Are there other question words that have だけ in them?

Yes. At least the following: - これだけ - それだけ - 及ぶだけ - 出来るだけ

As the above dictionary link mentions, remenants of take can be found in words なるたけ and ありったけ.

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    Is it the same with 好きなだけ meaning as much as you like?
    – rikijin
    Apr 12, 2013 at 13:44
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    @rikijin Yes. Also, notice that 好きだ becomes 連体形 好きな which だけ attaches to. This is a result of derivation from a nominal take. You would expect 連体形 before any attaching nominal, such as in 好きな人, 好きな食べ物 etc.
    – Dono
    Apr 12, 2013 at 13:56

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