I guess I'm thrifty and can't understand how people can spend up to $500 per night for a hotel room or suite.........
I didn't grow up that way, therefore I'm not used to spending that much for a hotel room.
That's how we feel about it, too. I can afford $4000 for a week at OKW, but I would never pay it. We own a vacation condo in a ski town and trade weeks all over the country- this time it's OKW. But, I'm paying on a mortgage which is an investment. I realize this answer is not for everyone- but even a timeshare might be a reasonable thing to look at over the long haul.
We also utilize business (conference) travel quite a bit. At least the room & one airfare is paid for then.
The other thing we do is accumulate points by charging everything on a Wells Fargo Mastercard, which allows us free nights at a Hyatt or Marriott, and free car rentals. FF miles are essentially worthless to us because there are so many of us- inevitably the "free" seats are on flights that are so expensive for everyone else it cancels out. Priceline is a great way for us to get airfare- they love selling 5 tickets at a time.
Finally, read this article: http://finance.yahoo.com/expert/article/millionaire/20382
Anyone can live beyond their means, we are no different. I figured out what the problem with our spending/saving by keeping track of it through Quicken. It is unbelievable how much money we waste- before you say you don't- read the article. We saved thousands of dollars in 2006 buy cutting out all the little crap. It's not vacations that break the bank- it's that daily latte, bagel and newspaper.
For me I use direct deposit to a money market account every paycheck. I normally bump the amount up by $25 every so often, this forces me to adjust my budget and spending habits. I now save $350 per month strictly towards the vacation fund. Other than that I use a lot of the same strategies as others. Great money saving tips on this thread. 

Anyway, another way I pay for this is by never spending change. Whenever I break a dollar bill, the change goes into a jar at the end of the day...it adds up really fast!! And the third thing I do is use a "rewards" credit card to pay for all of my day to day expenses and many of my monthly bills to get free airfare. But, AND THIS IS IMPORTANT, I still write down all transactions in my check register like I would if I was writing a check or spending cash so I never spend more than what I have in the account, and can therefore pay off the credit card in full every month with no interest.

