The hotel industry is ever evolving. What I do not get especially in the US is the fact that many of the mega Hotel chains such as IHG, Hilton, Starwood or Marriott sit on such huge amount of prime real estate and yet they would rather let their rooms empty rather than give you or me some free rooms :)
Anyhow, this industry had one of the worst loyalty programs which were revamped for the better in recent times, towards the end of the decade. I would not recommend accumulating any of the hotel chains points for long time. Few months would be a good exit point. There are some credit cards which partner with various hotels. But do not expect any gift card redemption option or sensible airline point conversion. The only exception to this rule is the Amex Starwood preferred card. Which is surprising, given that it is a hotel card at its core but seems to integrate well with airlines. The drawback is of course the hefty annual fee on this card. Another good option is the Wyndham credit card. I stick with Hilton or IHG (Holiday Inns) though I do go to Marriott at times along with other hotels depending on the deals.
So, credit card wise the best would be the Chase cards, Amex cards and the US Bank driven Wyndham cards. Hotel redemption wise, in the US, the best options are the Marriott and the IHG. Wyndham is decent and so is Hilton. Internationally, Hilton and Marriott have strong presence at multiple locations. Starwood is something that you could apply in a targeted fashion if your travel destination has significant presence of this chain.
In the Asia/Europe/Africa sector, you are bound to find a good amount of Hilton/Marriott properties. Australia is a different game while Canada has options very similar to the US. For South America, I would stick with known brands such as Marriott. There are lot of franchising and local corporate-run chains which tend to significantly dilute the service of other well known brands.
Finally, I think once in a while, one must experience very high end hotel stays. Westin is one such which is pretty much a good example of what a high end hotel has to offer. There is of course a lot of niche hotels which cater to the high heeled but in my opinion, it is better to not make an ass of yourself or come off as a cheapstake by bargaining about hotel points in the lobby of such big hotels. Usually, one is better off if a business sponsors you to the higher end of the hotel chains and get you reimbursed. The point redemption options here are not there or are simply not worth it. The business model of really top notch hotels depend on service and margin and is really not loyalty focused. You would pretty much find yourself in needless arithmetic when you enter this zone.
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