What works for me is dividing every paycheck I have into various funds: regular expenses, retirement savings, college savings, charitable giving, saving for the next car, vacation (yeah). That means ahead of time I have decided how much money to allocate to what and I feel very free to spend the money allocated to a fun frivolous thing like vacation on that. I also already have an emergency fund funded. That means I'm covered for everything that is important to me and am free to have some vacation fun.
A budget not only helps spenders save, but also helps savers spend! And I fall into the later category.
Everything in the vacation budget goes to vacation and the fun part is deciding where to go and how to spend that money.
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What I have had problems doing though is booking things that I saved the money for that seem overly extravagant and did't seem like that great a value. I think I'm going to do them, but then change my mind and instead do maybe two or more modest vacations instead that I know my family will love that seem to have more bang for the buck.
(e.g. Alaskan Cruise with balcony and expensive excursions -- just couldn't spend the money // instead did a week in Colorado, a five day trip to LA/
Disneyland and a Manhattan extension to a trip out east when we visit relatives. And these three things combined came out to be $4000 less than what the cruise and excursions would have cost.)
Also for Disneyland, I was looking at the Grand California and Disneyland Hotel, but in the end just couldn't spend that much money and instead am staying on Harbor Drive at the Camelot Inn in a suite (10 minute walk to main gate)