I like to think of traveling as one of my favorite hobbies, and I know as well as anyone that this hobby happens to be a huge money drainer. A few relaxing weeks can quickly become thousands of dollars before you've even left your house. Money is probably the biggest deterent to a lot of people traveling (or at least, this is what I tell myself. Because why else wouldn't you want to travel?). One thing I refuse to skimp on is the activities, because if you're not going to visit the sites you want or do the activities you want, what's the point of being there?
So that leave a few things: accommodation, flights, food, and transportation.
Quite possibly the most important thing you need to do is set a total budget, then divide that by the number of days and work out what you have to spend on what. Once you start working out what you need to spend money on you realize that what may seem like a lot may not get you very far.
The first thing I do is look on discount hotel sites. Unless you're staying in a hostel or couch surfing (both good options, but not for me personally) you probably are going to be staying in a hotel. Sites I've used include hotels.com, laterooms.com, and lastminute.com. It's important to check a few different sites because often the same hotel will come up with different prices depending on where you're looking. It also makes searching quick and easy since you can pull up loads of hotels in one area, compare prices and see pictures of them all. Another great site I've discovered is hotelyo.com. They have huge discounts, often on really nice places in great locations. The only problem with this site is that there are only limited number of locations available at one time so this would be great if you are lucky enough to find where you want to go or are just looking to get away and don't mind where you go.
If you have the option of traveling in the off season and during the week, you can save a lot of money on the hotel. Actually a lot of cities are wonderful to visit during the off season as you avoid both the crowds and the extremes of the weather. If you're lucky enough to be able to travel during the low season, definitely take advantage of it.
Extra tip: If you are walking into a hotel on the day without a booking, often they will lower their price slightly to give you a deal (don't ask for too much of a reduction, $20 tops) since selling a hotel room at a slightly lower price is better for them than having an empty room.
Let me know of any other tips you have for getting great deals on hotels.