- Tommy Obenchain
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- How to Get the Most Value Out of Hotel Points
How to Get the Most Value Out of Hotel Points
(Even at Less-Exciting Properties👇🏼)

Friends,
Hotel points get a lot of attention for the aspirational redemptions — think overwater bungalows, luxury resorts, and $2,000/night suites. But in my experience, the real value of hotel points sometimes shows up in far less glamorous settings.
And I write that as the guy who spent his honeymoon at the St Regis in Bali for free. Aspirational redemptions are out there, too—they are just not all there is.
Because sometimes a great use of points is the freeway-side Hyatt Place outside of Roanoke, Virginia. Other times it's a Marriott Courtyard by the airport that keeps you from spending $350 on a last-minute room. These aren’t Pinterest-worthy moments, but they can be incredibly rewarding — both financially and logistically.
Here’s how I think about it:
1. Stretching Points on Low-Cost Nights
World of Hyatt is especially strong here: 5,000–8,000 point redemptions for Category 1 and 2 properties can save you $150–200 per night. Even if it’s not a dream stay, that’s 3–4 cents per point in value, which is stellar.
Marriott’s dynamic pricing makes it harder to predict, but even basic properties often yield 0.7–0.9 cents per point — a solid trade if cash rates are inflated (think major events, holiday weekends, or peak travel dates). My family used 17,000 Bonvoy points for a room at the TownPlace Suites in Monroe, Louisiana this past winter — which I found highly preferable to spending $200 for the night.
2. Avoiding Nonsense Resort Fees
Points bookings at most Hyatt and Marriott properties waive resort or destination fees. That $34 daily “amenity charge” in Orlando? Gone. In many cases, this benefit alone makes using points a great deal.
3. Elite Status Sweeteners
Even at modest properties, status helps: late checkouts, room upgrades, and free breakfast go a long way. Marriott Bonvoy Platinum or Hyatt Globalist status can turn a basic stay into something smoother, even if not luxurious. The Hyatt Regency in Birmingham is a favorite of mine (lol) — they take great care of Hyatt Globalists.
4. Booking for Others or Bridging One-Night Gaps
Points can be great for gifting stays to friends and family, or covering a one-night stay that splits longer travel.
Big Picture: You don’t need a Maldives fantasy to make hotel points go the distance for you. Used thoughtfully, even the “less exciting” redemptions can create huge value — and a lot less financial friction in the day-to-day of real-life travel.
One quick note before I close: I did end up applying for Frontier Gold status this week. The promo is still live through midnight tonight (4/30).
My newly minted gold status is valid through December, and I have no idea if it will be worth the $40. But they fly nonstop from Dallas to a few cities where I have clients, and it gives me an excuse to actually give them a try. Free seat selection, early boarding, and a carry-on included? We will see if it is better than flying Spirit.
Do I expect to come back here in a few months and tell you Frontier was a revelation? No. But I am excited to (hopefully) report on the Frontier experience soon.
Fly well.
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Links
Slightly dated but great bit on airline status and loyalty programs.
Royal Caribbean — wow.
Super interesting write up on AI usage at United.
I mean this is just wild: the King of Thailand is 737 type-rated.
Remember, this life you are living has meaning. Thank you for reading. I am grateful you are here and would love to hear from you. If you'd like to write me a note, simply reply to this email. Otherwise I'll see you in the next one.

P.S. If I can ever help you plan your next travel adventure (slash help make your points go farther), I’d be delighted. You can schedule time together here.