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There are a number of current Amex Offers with Hilton offering between $35-$50 back depending on chain and spend. Those offers might be stackable with a Slickdeals rebate good for $30 back on $300 or more at Hilton, increasing your savings to up to $80. If you can pull off a double stack, you might save as much as $100 on a $350 stay. You should also be able to take advantage of Hilton’s Double Up promotion for double or triple points this quarter, coming out to a nice savings on a Hilton stay.
As you can see, those deals are each good for rooms booked direct and on bills of $175-$250 depending on the chain. The terms indicate that you must book direct with Hilton / Double Tree / Hampton Inn / Hilton Garden Inn. In my past experience, booking through Hilton.com has worked for all of those offers.
In addition to the above savings, there is a current Slickdeals rebate good for $30 back on a $300 Hilton booking if you book by 10/10/17 and stay by 12/31/17. Note that this rebate is valid only on hotels within the US (which I believe also applies to all three Amex offers) and there are some specific property exclusions. You’ll want to see this Slickdeals thread for more information / exclusions and to use their link in order to qualify for this rebate. This will not stack with a portal as you’ll have to use the Slickdeals link, so be sure to compare against portal cash back rates through CashBackMonitor.com. At the time of writing, the Slickdeals rebate works out better on a stay that is exactly $300 or slightly over.
The best way to maximize this one would be to find a Hampton Inn or Hilton Garden Inn stay that rings in at exactly $350 with tax (and over $300 before tax). You could then theoretically split tender on payment and use two cards that are both loaded with the $35 back on $175 offer for a total of $70 back from Amex (See: Complete Guide to Amex Offers for more information on adding an offer to multiple cards). Then, fill out the rebate form for $30 back from Slickdeals and you’ll have gotten $100 back on a stay of $350. And that’s before accounting for the value of the double / triple points being offered by Hilton, which you would get based on the full pretax cost. Say what you want about Hilton’s poor math skills (and Travel Update had some more to say about that today!), but the math on this one might work out for you.
Stacking offers here will yield you a decent savings on your stay. While the Slickdeals rebate works out well on stays that cost right around $300, check out cash back portals and compare rates if your stay will be more.