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The Elder Scrolls V: Skyrim Hints
(Optional) Obtain the key to Margret's room.
1 of 3: Ask Kleppr if he has the key to Margret's room, then try to persuade or intimidate him into giving it to you. If that fails, you could bribe him to get it.
2 of 3: Another alternative is to sneakily steal the key that's on a shelf behind the counter (on the west side).
3 of 3: Or you could pickpocket the key from Kleppr or Frabbi.