Travel is all about dollars and cents with me. I guess it depends on who actually buys these vacation packages....which i never do (I have undercut every one of those packages in the past by using airfare sales, priceline, and vacation rentals)
Many people, including myself, continuously eyeball a "dashboard" of destinations. If SoCal is $600 for airfare one date range, and boston is $200, i'll just go to Socal some other time.
There is a culture of impulsive buy last minute getaway travellers, and those people do understand what the fair market price is for a particular destination. Right now, its a completely convoluted process...especially dealing with the airline. Yes, fare calendars do help, but thats just the tip of the iceburg.
One of the most interesting implementations I have seen is farecast's USA/Europe destination map with best prices for bargain dates within a range. They are not the only ones. It could also be a list.
There is a picture of a teepee on the search screen. Is that an actual destination or stock imagery?