Recently I won $2000 in a costume contest put on by a radio station and new travel company. $1000 in cash from the Radio station and $1000 to use on the travel company's website to purchse a trip. My question is: how much am I going to be taxed on this money at the end of the year? They won't withhold taxes for me so I want to plan in advance so I don't get hit hard at the end of the year. I make about 45K a year at my job. Could anyone help me? And just for those who are curious I am going to Jamaica with my girlfriend for a week.....ahhhh the pampering.