If you’ve ever paused during checkout wondering, “Should I book this hotel with cash or points?”, you’re not alone. It’s one of the most common dilemmas among frequent travelers—especially those chasing every last drop of loyalty value. And the truth is, the answer changes depending on where you’re booking, the date, the program, and how much your points are really worth.
But one thing’s for sure: you shouldn’t be guessing. With smarter tools like Gondola and better timing, you can ensure your redemptions—or cash bookings—deliver maximum value every time.
Don’t Hoard Your Points—Spend Them Regularly
While it might seem smart to save your points for a future dream trip, holding onto them too long can actually work against you. Hotel points often lose value over time due to several factors:
- Devaluations: Loyalty programs can increase redemption rates without notice, meaning your points might suddenly be worth less.
- Dynamic pricing: As demand increases, so do the points required for a stay—even if the cash rate doesn’t change.
- Inflation: If hotel prices rise faster than the value of your points, your redemptions won’t stretch as far.
The bottom line? Use your points when they offer strong value—because tomorrow, they might not go as far as they do today.
Booking with Points Often Comes with Hidden Perks
Booking with points can save you more than just cash—it can also unlock extra benefits that don’t always apply to cash reservations. Many hotel loyalty programs include perks that make points redemptions even more valuable:
- Hilton Honors: Waives resort fees when you book with points and offers a 5th night free on five-night award stays.
- Marriott Bonvoy: Offers a 5th night free when booking entirely with points.
- World of Hyatt: Waives resort fees on points stays.
- IHG One Rewards: Provides a 4th night free for IHG cardholders booking with points.
- Wyndham Rewards: Earns at least 1,000 points per qualified stay booked with points.
These benefits—waived fees, bonus nights, and extra perks—can quietly tip the scales in favor of using points, even when the point value and cash price seem close.
Let Gondola Do the Math for You
Instead of dusting off your TI-89 calculator, Gondola does the math for you—automatically comparing the cash rate, the points rate, and the true value of each option so you can make the smartest decision for your stay.
Say you’re planning a ski trip to Aspen and comparing two properties:
🏨 Property 1: The St. Regis Aspen Resort
With a cash rate of $2,695 per night—well above average for the dates—redeeming 146,000 points gives you a value of 1.85 cents per point, an excellent use of Marriott Bonvoy points.
🏨 Property 2: W Aspen
Though both the cash rate and points required are lower, the value comes out to 1.58 cents per point. Not bad, but not as strong as the St. Regis. If you’re aiming to maximize point value, the St. Regis is the clear winner.
With Gondola, this type of side-by-side comparison is seamless—no manual calculations required.
If You Choose Cash, Booking Through Gondola Earns You More
Sometimes, cash is the smarter move—and when that’s the case, booking through Gondola ensures you earn the most possible back. Here’s how:
- Earn hotel loyalty points (since your reservation is made directly with the hotel)
- Stack credit card points
- Get 3%+ Gondola Cash back, redeemable toward future travel
When all those layers are combined, you can get over 16% back in total rewards—making a cash booking through Gondola often just as valuable, if not more, than redeeming points.
Final Thought: Don’t Guess—Know
There’s no universal rule for when to use points or cash—it all depends on context. Use points when you’re getting strong value, cash rates are high, or your points are nearing expiration. Choose cash when redemption value is low or when you can stack significant rewards with Gondola Cash and elite benefits.
Gondola can make all the difference when making these decisions. It removes the guesswork by showing you, clearly and objectively, which option delivers the best return—so you can book confidently and get the most out of every stay.