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Or, if the blockade is too powerful, it might just block up the entrance entirely (or rig it with traps and wait for the PCs to get curious and come inside to investigate why no more drow are coming out). In this case, it could easily switch to a new access point - or even dig new ones. Such a settlement could prove extremely difficult to block off entirely, as it could easily break off into new settlements without the players even being aware of it. If the AI was smart enough, it might even leave a few drow as a decoy before moving off somewhere else. Imagine camping outside the Drow city only to suddenly receive shouts of help from the rest of your guild - because the drow had launched a counter-attack against your guild HQ!
In addition, a well-situated settlement could hold out even longer - for example imagine a settlement beside the ocean, which could continue to trade with other settlements even when under seige (or "camped out") by PCs. Or the dwarven settlement which existed both above and below ground, and could simply continue expanding downwards (although admittedly at a slower rate). Even a settlement beside a river might be able to sneak supplies in and out.
If you wanted to get really smart, the settlement might try sending out diplomats to bribe some of the players, or assassins to take out the guild leaders.
Then there's magic, of course. An "undead settlement" (ie a powerful necromancer/lich controlling an undead legion) wouldn't need food, although it wouldn't be able to expand much without new bodies. Other societies might have mages who could create magical portals for bringing in supplies - not only would the PCs need to block off the settlement (hardly an easy task), but they'd also need to magically ward it off. Now the settlement only has to strike at one location and hold off the PCs long enough to break the ward in order to get supplies through.
In addition, there are other problems associated with blocking off a settlement - famine has been mentioned already, but the other big problem is plague. A group of staving diseased goblins are unlikely to put up much of a fight, but when half the guild goes down with the plague it's going to be a serious problem.
If the settlements match with player races, you could also introduce bounty and reputation systems. A guild which blocked off a drow settlement could get a "bad rep" with the drow - and drow PCs might earn a reward for killing members of that guild. There's invariably going to be some particularly strong PC members of each race (and some weak members of each guild) which means that any guild which deliberately camps out around a settlement is going to start losing guild members to PK. If the guilds are race-based (and particularly if the settlements are sometimes player hometowns) such activities are quickly going to turn into PvP wars. Camping an entire settlement is going to be hard enough, but when that settlement is the home of another guild it's suddenly going to become a LOT more difficult.
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