Yes, and no. Or yes, OR no.
Depends on the pedals, how many of them, etc.
Here's the short version--
Magnetic guitar pickups output a weak high impedance, low level signal. It's VERY susceptible to interference/noise, so must use a shielded cable.
Shielded cables have inherent cable capacitance-- this will vary somewhat by the brand of cable, but certainly by the LENGTH of cable. About 18' or more of typical cable and you can start to notice a difference at frequencies of interest.
Now, with that as background information...
"Bypass" doesn't always mean the same thing in a pedal.
Sometimes it's a mechanical "hardwire" bypass (or "true bypass"), meaning that the switch bypasses the pedal circuitry as though it weren't even there... the guitar signal is completely routed around the pedal circuitry. This is usually the "boo-teek" option, and the theory is that this is the "best" way... but theory and practice is not the same, and it's not that simple (more later...)
Some other pedals implement a buffer in bypass mode. Instead of a completely passive hardwire bypass, the signal is instead routed through a simple buffer amp. This lowers the impedance somewhat, but otherwise theoretically leaves the signal unchanged. What's the advantage of this? I'll get to it later. But suffice to say that some buffers are very well-implemented, and others less so.
Finally, some pedals have a cheapo passive bypass scheme where they simply give the straight signal a "path of least resistance" around the pedal circuitry, but the pedal's circuitry can still present a partial load to the pedal. Older wah pedals, many older fuzz pedals, etc are like this. This is generally "no good" and can audibly change the sound (guitarists call it "tone sucking"). These are usually best modified for true hardwire bypass.
If you have a 10' cable, one pedal, and then a 5' cable to the amp, hardwire "true bypass" is probably a good way to go. It won't sound much different than straight wire in these circumstances.
However, if you have a 10' cable, five pedals each with 1' of cable between them, and then a 15' cable... you will want at least one buffer in your chain. If you have nothing but "true bypass" pedals your sound will be noticeably impacted for the worse. That's a lot of cable capacitance, even with superior-quality cable. Lowering the impedance of the signal with a buffer will help negate the influence of the cable capacitance on your sound.
Hope that helps.