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The Dungeon Master's Guide, on page 187, says:

Placing a portable hole inside an extradimensional space created by a bag of holding, Heward's handy haversack, or similar item instantly destroys both items and opens a gate to the Astral Plane.

A portable hole is a "similar item" to another portable hole.

Thus, if one puts one portable hole inside another portable hole, they are both destroyed, right?

The rules about combining extradimensional objects seem to be very strict in 5th Edition, but this rule seems to be vaguely worded. I guess the intent is to discourage the use of combinations of extradimensional items, and to punish careless players.

If, on the other hand, there is some reason to stress that each item is only incompatible with items of other designs, then the rule means that each portable hole is compatible with every other portable hole.

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  • \$\begingroup\$ related: same question, but for bags of holding \$\endgroup\$ – nitsua60 Jul 18 '16 at 20:08
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    \$\begingroup\$ @Akixkisu Please slow down on the edits. Currently more than half the front page is being bumped by them, which is overshadowing newer content and other actions in need of review. Pace yourself. Aim to limit yourself to, say, a dozen edits on the front page at any one time at most. \$\endgroup\$ – doppelgreener May 13 at 11:49
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    \$\begingroup\$ Ask on meta if you have questions; for this comment thread it’s probably enough that a mod done told ya, don’t you think? \$\endgroup\$ – mxyzplk May 13 at 12:58
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Yes, a portable hole is a "similar item," and when put into another portable hole will destroy both and create a planar rupture.

It's the "nesting" of extradimensional space that causes the havoc, not any properties particular to these magic items individually or as a set.

Note however that there is something particular to the kind of extradimensional space attached to these items: the nesting problem only manifests relative to extradimensional space created by such magic items. They'll all play havoc with each other, but you don't have to be paranoid simply carrying such items into other planes, pocket dimensions (natural or spell-created), and the like. Whatever space these items connect to, it's not the kind of space you can wander into unknowingly while planeswalking.

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    \$\begingroup\$ Maybe you don't have to be paranoid while carrying your portable hole into a spell-created demiplane, but I think you still have to be paranoid. E.g., the player can routinely use a portable hole for storing loot. The DM can give the players a locked, lead-lined chest of drawers which looks nothing like a bag of holding. The unsuspecting players can put this chest into the portable hole - but the chest contains a concealed bag of holding, so all the loot in the portable hole gets destroyed. This retains the adversarial flavor of AD&D, which is probably the intent of the rule. \$\endgroup\$ – Rick Jan 31 '15 at 0:38
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    \$\begingroup\$ Yes, there's no reason to be paranoid except when the universe is actually out to get you. (I only mentioned the bit about planeswalking because I wanted to emphasise that an extradimensional space and a pocket dimension are different and don't interact destructively; a situation more likely to come up across many DMs' campaigns.) \$\endgroup\$ – SevenSidedDie Jan 31 '15 at 6:11

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