The Bermuda Department of Tourism and JetBlue have teamed up for the Feel the Love sweepstakes. I like this one because it doesn't rely wholly on chance. However, you have to have been to Bermuda at least once already, since you'll need to submit a memory and photo to enter.
The contest runs through May 31. Entries should fit into one of four categories: family, sports and adventure, romance, or rejuvenation. The vacation package prizes include airfare, accommodations, and extras such as dinners, childcare, or massage, depending on the category.
Priceline is running a promotion as well, though this one doesn't offer the thrill of the win or the agony of defeat. Through March 23, when you book a room at a hotel participating in the published-price hotel reservation service, you'll get $100 to put towards a Priceline vacation package of four nights or longer.