Originally Posted by
Sixth Freedom
It is possible to save a great deal of money.
I would suggest that you focus on saving money on airline tickets as hotels are relatively cheap but air travel, particularly in premium cabins, is very expensive.
Not always true. 2009 saw some of the cheapest airline deals (Europe to Sydney for £1,600 in flat-bed business, for example) ever, but hotel rates held up as hoteliers generally tried to keep pricing up even if volume was lost.
I wouldn't transfer hotel points to airline miles except as a short term top-up to reach an award threshold. Once you've saved £1,000 on a holiday by getting the flights on miles, you can save another £1,500 by getting a weeks luxury hotel for free if you work the hotel schemes properly.
(Although, OP - the Hilton scheme is now probably the worst out there given they now want 50,000 points for a top property - and many of those, at least in London, are still dumps.)