One of the biggest internal struggles in travel is that tug-of-war between wanting to pay the least amount possible… and realizing that spending a little more might make your life a lot easier.
Years ago, this became such a recurring issue for me that I came up with a personal guideline — my $15 rule — which basically says: if a small charge will noticeably improve my travel experience, just pay it. Don’t overthink it. Just pay it.
This all came to mind again recently when I was booking a stay at a Marriott Bonvoy property, and found myself fighting with the system — and with myself.
Booking the Stay
We had a couple of 50K free night certificates from our Marriott Bonvoy credit cards and found a Courtyard that seemed like a decent use, decent being the key word here. Marriott no longer uses award categories, so pricing is dynamic and changes constantly based on demand, brand, and whatever algorithm controls the Bonvoy machine.
The nightly cash prices ranged from around $120 to nearly $180 on this particular weekend. It’s not a fantastic value for a 50K cert, but it’s still better than letting one go unused. Breakage is real, and programs are counting on it.
That is, until I tried to actually book the room.
In the past, Marriott allowed you to combine different forms of payment — cash, points, and free night certificates — and even mix and match on a per-night basis when booking online. That functionality was quietly removed on January 16, 2025. Now if you want to book a stay using multiple payment types, you have to call reservations and ask them to piece it together for you.
For this particular weekend, the best option would’ve been:
- Thursday: Use a certificate
- Friday: Pay cash
- Saturday: Use another certificate
If I could book that setup online, it would’ve been easy. But since I couldn’t, Marriott wanted me to pay the full standard rate for Friday as part of the combined booking — no AAA discount, no special rate. However, booking Friday separately would have saved about $25.
What Could I Have Done Instead?
I could’ve made three separate bookings:
- A certificate reservation for Thursday
- A separate AAA rate booking for Friday
- Another certificate for Saturday
Then I’d call the hotel and ask them to link the reservations. Hopefully, we wouldn’t need to switch rooms mid-stay, and maybe — just maybe — not need to visit the front desk daily for a new key.
Did I Mention I Wasn’t Going?
This wasn’t even my trip — I was booking it for my wife. And while I enjoy wringing every last cent of value out of points and perks, she prefers a much simpler approach: check in once, get a room, enjoy the stay, don’t deal with Marriott’s quirks.
So in the end, I made a single booking using two certificates and paid the slightly higher rate for the cash night, even though I could’ve saved money with a more complicated setup.
Why? Because keeping things simple was worth the $25.
Final Thoughts
This booking made me face some decisions I often have to make for our travels.
- Am I getting a good value for my points/free nights?
- Is there a cheaper way to book this reservation?
- Should I just pay the extra money to make it more convenient?
This time, simplicity won. I used two certs, paid a little extra, and avoided a multi-reservation mess and a phone call to Marriott — all in the name of convenience and domestic harmony.
And sure, I could’ve squeezed out a few more dollars in value. But sometimes, it’s OK to pay more to keep things simple.
Because, as we say… Your Mileage May Vary.
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This post first appeared on Your Mileage May Vary
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