I find hotel loyalty to be extremely complicated. This post essentially bares the question are you an occasional holiday traveler or are you a business road warrior? For a road warrior, elite hotel benefits such as complimentary wifi, room upgrades, late check out and breakfast make a huge difference. For the occasional traveler, you get what you pay for and saving money is far better than flashing a hotel elite card at check in. Whereas with an airline ticket, you receive miles for most any standard purchase through any site; with hotels there are many stipulations required to actually receive points or an elite credit. Not only are points and miles at stake, depending on your booking source, so could be hundreds of dollars.
If you are a road warrior, top tier elite status with programs like Hyatt and Starwood are worth it. Each offer insane benefits and a portfolio of business and luxury vacation properties, which turn your business perks into free stays on vacation. Elite status helps, but the less you travel, the less the benefits actually benefit you. I receive Starwood Preferred Gold through my American Express Platinum Card and there are many hotel co branded credit cards that offer a free night and mid tier elite status, if it weren't for that I would never bother attempting to attain it. I would rather save the money by booking through a discounter than earn middle or lower tier status at Marriott, Hilton, Starwood, IHG. On the other hand, if I had a busy travel year I would go out of my way to earn Hyatt Diamond status, which comes with club level access (free food), the best available room at check in, four suite upgrade certificates, food credit or points bonus at check in and true VIP treatment. If you are a road warrior, I'd look into their Diamond fast track challenge when it returns ; )
Whichever end of the spectrum you are, window shopping is essential. In major cities it feels like there are more hotels than people. I enjoy using TripAdvisor to create a potential short list and rough pricing guide. Once I have my shortlist I cross check those rates with Expedia, Amex Travel, Ebookers, Travelocity, Priceline, etc and finally with the hotel itself directly. Direct booking almost always receives elite credit and unique benefits. While comparing hotels in Rome, I found that if booked directly, the hotel threw in a bottle of wine, late check out and for stays over three nights, a complimentary dinner for two. The difference in price in this case was too high to justify, but in many cases it can be well worth it for the elite credit and perks.
As with most everything I write, this post isn't going to change your life, but it will hopefully change the way you approach planning and booking your travel. If you're anticipating a busy year, make the most of it by receiving benefits on the ground and in the air. If you are an occasional traveler, don't just take the first price you see as gospel. Sometimes rooms are contracted to a specific vendor and a five star on one site might be cheaper than the best four star on another.