3. Consider Several Options
Rather than just researching airfare and hotel separately, look into packages or even all-inclusive vacations. Also, consider vacation rentals. Not only can you get more for your money (an entire house, perhaps, for what a hotel stay would cost), but property owners get nervous if they aren't fully booked, and this can lead to some great deals. If there are limited or no bookings on a property's website calendar a couple weeks out, email the owner to see if he or she is willing to negotiate on rates. If a place is fully booked, don't despair. Ask the owner to put you on a cancellation list; if someone backs out, you'll probably be able to get a reduced rate.
4. Have More Than One Strategy
Sometimes when you see a deal, you need to grab it. The sell-off vacation competition is keen, and he or she who hesitates loses. Other times, a slower strategy might pay off, such as booking two weeks in advance to secure a good price on a vacation rental (though not necessarily on airfare). Regardless, part of your strategy should be booking on Tuesday or Wednesday. Generally, by midweek, accommodations and airlines know how well booked (or not) they are for the upcoming weekend and will begin to offer deals if business is slow.