Meanwhile, I often hear from friends... "I'm going to (fill in the blank city) and I know you've been there. Where should I stay and how do I get a good deal?" If I've been there, I'm happy to give specific information. If not, here's my standard method for finding a good deal.
First step - I go to www.sidestep.com. What I like about Sidestep is that, unlike Orbitz or Expedia, it is not a booking engine. It is merely a price comparison. It shows you more airlines than the 2 afore mentioned and it tells you where to get the deal (i.e. on the airlines' site, or cheapoair, or orbitz, etc).
Second step - once I find a flight combo and price I like, I go to the airlines' individual sites and search there - as well as other booking sites, to see if other times or web only fares are listed. On both Sidestep and the individual sites, I search both round trip and one-way flights... since sometimes it's cheaper to book one-ways on 2 different sites than a round trip with one airline.
For instance, I prefer JetBlue to NYC, but sometimes I need to give up the TV and fly only one way with JB and the other with say, Continental. I also will fly into JFK and outta Newark, or vice versa, if it's cheaper and if the times work better for me. Not a big difference in cab fare. And, in certain markets, I find that you have to figure out who the best carriers are for your connection and shop those (for example, United and US Air are the 2 best choices for me, with regards to price and non-stops/directs, from Fort Myers to Reagan National in DC).
Travelzoo is my favorite for hotel deals and is always my starting point. I receive their weekly Top 20 Deals list and it prompts me to browse my fave cities. Sometimes I create a trip based on a deal, versus picking a date then finding a deal. I like Travelzoo because there are some independent properties and small hotel groups that I have found I can rely on for periodic Travelzoo exclusive deals. Like for instance, one of my fave hotel groups, Kimpton, will post Travelzoo deals. To date I've stayed at 4 of their properties in NYC, San Fran and DC....all with Travelzoo deals. When I had the Hawk's Cay Resort account, we did Travelzoo promotions as well. You have to check back regularly on Travelzoo, because the deals come and go and book quickly... kinda like shopping at Costco or Homegoods.
I will shop hotels.com, because they sometimes have a sale on certain hotels. BUT, I only book hotels I am familiar with or have read reviews on TripAdvisor. I think that sometimes their 3 star or 4 star hotels are more like 2's in my book. Prime example, The Paramount in NYC. Not horrible, but not great and the rooms are the size of a walk in closet.
I also like to follow Budget Travel's magazine and website for deals and recommendations. They often write about hotels you would never find on any major booking site like hotels.com. Mostly hotels with a large inventory on rooms will appear on hotels.com, esp in major markets... so check out places like budgettravelonline.com for smaller boutique reviews and deals. I have had some success with Marriott's website, and I also receive their members e-mail with last minute specials.
My best tip on hotel bookings, if you find a deal, check the cancellation policy and the rez requirements. If you can cancel up to a day or two prior and they only do a credit card hold, then by all means, book the deal and then keep shopping for a better one!
I don't do these very often, but one great tip I learned this summer from a good friend... if you are booking a car for a long period of time (esp one way), try shopping it with shorter rentals. My family went on a cross country for 3 weeks this summer, and instead of renting a car from Kansas City to San Francisco for 3 weeks, we did 3 one-week rentals (Kansas City to Jackson Hole, Jackson Hole to Vegas, Vegas to San Fran) and saved over $1,000 dollars. With the same company! I kid you not!
I like "This Just In" by Budget Travel and receive their RSS feed.
I'm open to any great deal finding techniques you have... please share!