Win One of 52 Trips with the Hilton Ultimate Weekender Sweepstakes

Hilton Hotels often runs sweepstakes, but The Ultimate Weekender is a little different from most. It’s running throughout 2014, until January 2, 2015, and there are several ways to enter and win one of the 52 weekly prizes. These vary each week but generally consist of 2 free nights at a Hilton Hotel, 100,000 American Airlines miles, a $100 Hilton gift card, and a check for between $500 and $1,000. I don’t think the destination described really matters as far as how you redeem the prize, but this week is the “Big Apple Weekender.”

Hilton Ultimate Weekender

If you don’t win one of the weekly prizes, there will be one grand prize winner who wins enough free goodies to take one weekend trip every month for a year! This prize bundle includes 24 free nights, 1.2 million American Airlines miles, $1,200 in Hilton gift cards, and a check for $10,000.¬†Or you could just spend a whole month at the Conrad Koh Samui by using them all at once.

You can enter every week on the web site, plus get additional bonus entries by looking for a secret phrase on the Hilton Facebook page, sending a tweet, or interacting in other ways with Hilton HHonors. Additional entries may also be earned by staying at a Hilton. (A maximum of 52 entries are permitted for the grand prize.)

The entry methods and the specific prizes available each week are quite complicated, so you can read the full terms and conditions to learn more. However, it seems that there’s something worth winning every week so I wouldn’t worry too much about which particular week you happen to enter. You can enter at

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  • Dan Miller

    I think your link to the sweepstakes is broken

    • Scottrick

      Thanks! Fixed.

  • Alan

    It’s US/Canada only, Scott – might be worth flagging that up front. Looks like a nice competition too :-(

  • MSPpete

    Link to the sweepstakes at the bottom of the story is still broken. Oops!

  • A.M.

    Still broken – no where to sign up