My Starwood dilemma

I’ve heading to Hawaii soon and had enough points to book 8 rewards nights at a Starwood property. We are staying 9 nights so the last night I booked by paying for the room.

Originally the extra night reservation was for $380 – but after having read Loyalty Traveler’s post about getting a free night in New York City through Starwood’s Best Rate Guarantee – I decided to hunt for a better price for our room in Hawaii. I was finally able to find a rate on Travelocity for $250 pre tax and was able to use the Best Rate Guarantee to get a rate of $225 pre tax.

Now here is my dilemma. If I stay the 9th night on points instead of paying for the room, I will get the 10th night free as well per the “book four nights get the fifth free” rule. Our flights can be changed one day later with the same exact flights with no penalty.

It would cost me 31,000 Membership Reward points in essence for two additional nights in Hawaii.

a screenshot of a screen

I can’t decide what to do so help me by leaving a comment on what you would do? Is it worth that many Membership Reward points for two additional nights? I have Platinum status with Starwood.

Thanks in advance!


  1. I’m with most everyone else in saying more than 5 or 6 nights is too much for me but if you really like that sort of down time at one location then it’s worth the points for 2 extra nights. After all why do you collect the points in the first place? It’s so you can enjoy them. What a better way. Aloha.

  2. I would cut the trip to 5 nights. More than that is too many nights in one place. Heck, I’m never at home for 5 consecutive nights!

    Typing this makes me think I need help…;-)

  3. I would personally stay the extra two nights and now split up your trip between two islands 5 and 5. Hawaii is awesome 🙂

  4. sounds like a good marginal deal…However, as Matt said, 10 days is a long time, you will want a vacation from that vacation….I would pass!

  5. 10 nights in one place? Not my style at all, most of the time. Even at a great destination I’d often be ready to move on sooner, and the extra vacation day I’d have to burn to extend the trip would be a big factor for me as well.

    Are you richer in time or points/money/resources at this point?

  6. Happiness seems to increase the longer you’re there…we wished we had had one or two more days on our trip Jan ’12.

  7. It would help to know which island. For example 10 days in Waikiki is a too much. I would look for 2 book-4-get-5 deals at two different locations to get more from your trip.

  8. Are you staying on one island for this trip?

    If so, I would save those points and use them next year on a different island.

    No need to blow them for an additional two nights on the same island since each island has its own character worth experiencing.

  9. 100% worth if you have no other goal for your MR points right now. If you’re going to be there, have the time, and can change the flights, why not do it?

  10. I would do it if you haven’t already allocated the points for another expense. I was in Maui for 10 days in 2010, and there isn’t a day that goes by that I don’t think about that trip.

  11. Your already took the time to travel to the islands, no additional cost for the flight change and I can say with confidence you wouldn’t be dreading the extra night there. You are essentially paying 15,500 points per night for the extra two nights. Whatever you decide, enjoy your trip.

  12. No discount on the transfer? I Am getting 800 amex mr points for 333 *wood points. Others are getting 750 amer mr for their transfer bonus

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