You know sometimes you are just looking or a bargain. Times are tough now days and there really are some great deals to be had. I have found you can get some great deals if you are willing to wait to the last minute and be a little spontaneous. Some places also let you book your cheap vacation package weeks or month in advance. Its really up to you and your schedule and flexibility. Some great destinations offering great deals include Las Vegas, Atlanta, Hawaii and parts of Mexico. I would also check out the Caribbean but I have not been there personally so I can not give you too much advice
The best place to find deals are websites, newspapers or even your local travel agent. You can check out a ton of sites that even let you compare and rate different vacation packages. I would suggest starting at sites like Kayak.com, www.orbitz.com and even www.expedia.com. All of those sites offer great deals.