I've never really done this, but is it wise to wait until the last few days before a vacation to schedule things?

For instance, we are thinking of going one of two places (perhaps you've read about them in earlier questions I have had): New Orleans or San Antonio in March.

If I was to wait until say, three or four days before we need to leave, can I expect to get some cut rates on flights, hotels, cars, etc.?

Usually I have our plans for vacations pretty well mapped out several months in advance. But, for some reason, this time it's been harder for me to nail down good flights and accommodations at reasonable prices and in safe areas with good ratings by previous travelers.

Any help would be appreciated.

Flights - I doubt it as most rates seem to go up at last minute. 14 days out seems to be the closest you can cut it on fares on Southwest, for example.

Hotels- could get deals if there isn't anything big going on in the area at that time. We got our room in Las Vegas at a low price and then the week of our arrival, the price kept dropping until 2 days before arrival.

Cars - hit or miss, depending on supply.

If you are flexible on your destination it could work. ID a half dozen places you want to go and then see what deals abound. Chances are one will work out great. If you only have one destination in mind you might be left out.

Flights are the pricy variable. Do you have miles per chance?

You can go ahead and book hotels and then cancel if your plans change.

Maybe you could have one destination that is doable by driving rather than flying.

No miles. We fly usually with the carrier with the best deal at the best time that suits our needs.
I usually use Kayak, Travelocity or one of the other sites, so cancellation is not always a possibility.
It would be possible to drive to San Antonio (just under 900 miles), and it is less to New Orleans (700 or so). But with the price of gas and the time it takes, that might not be an option.
Thanks for the replies so far.
If anybody else has any ideas, please give me your reply.

Today many/most flights fly full - and waiting until the last minute will usually get you the highest prices, not the lowest. Unless you are going at a very unpopular time of year, hotel deals are often gone by then. In fact, often you get the best deals by doing non-cancellable internet specials several months in advance.

You MAY be lucky and find a deal - much more likely you are going to pay premium prices.