The Short Answer
Most often when the redemption rate implies a per-point value below roughly 0.5 cents, which is common at low-end award nights, or when redeeming forfeits a preferred-partner booking's amenities on a stay where the cash rate was already reasonable. Compare the cash price against points times your programme's typical redemption value before redeeming.
Loyalty programmes want a points redemption to feel like a discovery, a clever unlock of value you wouldn't otherwise access. Sometimes it is. Often the arithmetic, done honestly, points the other way, and the programme has no particular incentive to help you see that.
The only calculation that matters
Divide the cash price of the room by the number of points required. That gives you the value you're extracting per point on this specific redemption. Compare that number against your programme's typical redemption value, generally cited in the 0.5 to 0.8 cent per point range for most major hotel programmes, with real variance by brand and by specific award night. A redemption below that typical value is not paying for itself; it is simply spending points because you have them.
Where the maths breaks down most often
Low-end award nights at popular urban properties are the classic trap. A modest cash rate, say US$180, redeemed for 40,000 points implies a per-point value of 0.45 cents, below what most programmes' points are actually worth when earned through normal spend. You would come out ahead paying cash and keeping the points for a night where the cash rate is higher and the point cost stays flat, which does happen at many programmes on peak-demand nights.
Where redemption genuinely wins
The inverse case is real and worth watching for: a fixed points price against an inflated cash rate, typically at a small number of aspirational properties during peak demand, where the same point cost that looked mediocre on a Tuesday in a secondary city becomes an excellent trade against a holiday-weekend rate at a flagship hotel. Some programmes also cap resort fees or exclude them entirely on award stays, adding value the sticker price doesn't show.
The trade-off with preferred-partner booking specifically
A points redemption and a preferred-partner booking are mutually exclusive for the same stay, you either pay cash through the channel that earns you the amenities, or you redeem points through the loyalty programme directly, and award stays typically do not carry preferred-partner benefits since no cash transaction exists for the advisor's commission to attach to. Before redeeming, it's worth pricing what you'd give up: breakfast for two, a property credit, and a priority upgrade can easily be worth several hundred dollars on a multi-night stay, which should be weighed against whatever the points are actually worth if spent elsewhere.
Points redemption value is not fixed. It moves with the specific night, the specific property and the specific cash rate you're comparing it against. Any advice that quotes a single number for "what hotel points are worth" is giving you an average that may not apply to the exact night you're booking.
A rule of thumb worth using
Before redeeming, run the division. If the implied cent-per-point value clears your programme's typical redemption benchmark comfortably, and particularly if it exceeds it, redeeming is a reasonable trade. If it sits meaningfully below, paying cash, ideally through a preferred-partner channel that adds amenities at no extra cost, is very often the better outcome, and it preserves the points for a night where the maths genuinely favours redemption.
Our position
Points are not free money and were never designed to be spent reflexively. Treat every redemption as a specific transaction to be priced against its cash alternative, not as a default use of a balance sitting in an account. The programmes benefit when members redeem without doing this math; you benefit when you do.