Though most hotels are in the convenient but rather soulless Central Business District, Darlinghurst makes a better home base. It's walking distance from many eastern neighborhoods, it has good transportation options, and it's a destination in itself. The Chelsea is a pair of joined Victorian houses on a residential lane. Rooms are bright and spacious, and it's a value (chelseaguesthouse.com, en suite doubles from $110). For a CBD value, try the Blacket, which has minimalist decor at Target prices; many rooms come with substantial kitchenettes (blackethotel.com.au, doubles officially from $161, though deals do pop up). The recently renovated Hilton Sydney is a worthy CBD splurge. It has tons of amenities--including a massive gym--and the gadget-filled rooms are designed in such a way as to make a fairly small space seem larger (hiltonsydney.com.au, Internet rates from $184).
The Sydney Morning Herald Good Food Guide ($19) is indispensable for visitors who care about eating well--and you should!--with concise reviews of restaurants in every corner of the city; it's on sale everywhere. Luxe Sydney (luxecityguides.com, $9), as the title suggests, is upscale-oriented, but its "shopping itineraries" make excellent neighborhood walking tours for anyone.