Two step guide to Travel Cheap, but amazing.
1. The first step to planning a great vacation cheap, is to use travel points. NEVER buy anything without using a loyalty card that gets you points. They really add up!! But all points programs are not created equal. (You can consolidate points on www.points.com and see which ones are worth more).
The best HOTEL points program - hands down - is spg.com - run by Starwood Hotels (all the Sheratons, Westins, St. Regis and chic Ws). And it's free. You need about 7,000 points for free 4 star hotel nights anywhere in the world. The big secret is that you can also use 1,000 points and get an amazing room for a paltry $45 or $50 US in many cases! They'll also upgrade you for free once you arrive and show your spg card if there's a better room available. Starwood points are transferrable at a very good rate into lots of US airmiles programs. This is really  helpful if you're short points to book a flight on another awards program. Buying points is REALLY EXPENSIVE and most other points programs eat up most of  your points if you transfer them. (no I don't work for them!)

2. Learn how to use the on-line auctions. www.skyauction.com is a great site, as is priceline.com and luxurylink.com for very cool high end hotels. You can look on Luxurylink and identify a cool place to go, then hunt down the rooms on discount sites and book them there! Some of my favs are www.sidestep.com, www.qixo.com and www.orbitz.com. If you can't book a cheap flight from your city, use your points to get to L.A. or Denver, or New York or Miami and fly from there to Europe or Hawaii or the sunny south for a steal!