Sometimes these expensive house rentals turn out to be bargains because they accommodate so many people. This summer some friends and my family and I have a castle rented in Umbria - built by the infamous Borgia family - for a little under $1000 a night. It comes with two cooks, a maid, pool, tennis court and is on Lago Trasimeno. Because the place sleeps 14 it actually works out to be pretty cheap on a per person basis.

The most my husband and I have paid is about $450 a night for some of our sailboat charters. Fortunately most of my stays in what are supposed to be really expensive rooms have been free.