I'm 31 and never been on vacation in my life, I figure I should probably do it once before I die. So how the heck do you do it? I can find plenty of sites for airfare, but how do you find hotels at your destination? Do you have to call them up on the phone? I seriously have no f'ing clue what I'm doing, so if someone could help with the hotel part it'd be much appreciated.
Most travel agencies and travel websites have package deals where you can get flights, hotels and rental cars together. You can probably save money that way vs. booking each on your own separately. You don't need to call hotels directly. Expedia, orbitz, AAA.com, travelocity, etc. all let you book a hotel+flight(+car if you want).
The reason it can be cheaper to get a hotel+flight package is that it hides the actual cost of the hotel, so the hotel is willing to let rooms go cheaper than they would if the price was visible.
Read hotel reviews on tripadvisor.com first. Nothing worse than getting the cheapest deal and finding out when you get there you are stuck with a week-long non-refundable stay at a bad hotel.