How Gondola helps you decide when to book hotels with cash or points

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When it comes to stretching your travel budget, it's easy to optimize your flights by using Points Path's integration with Google Flights. But hotel bookings can be a little trickier — especially when deciding whether to pay cash or redeem points.

That’s where Gondola steps in. Gondola is a free hotel-booking platform that helps you make smarter decisions while earning up to an extra 7% cash back on every paid stay.

Gondola is an AI-powered direct hotel-booking tool that lets you compare pricing for your destination in a single, streamlined view, eliminating the need to open multiple tabs or rerun searches across various hotel sites.

It even pulls in the number of points required for each hotel chain — alongside the cash price — evaluating if you're better off paying cash versus redeeming points and showing you which option provides the better return. Similar to Points Path, it takes all of the guesswork out of the equation, helping you save points when cash pricing is favorable, or redeem confidently when the points value is strong.

To go a step further to help you maximize your rewards, when you choose to book with cash, you’re rewarded with 3% cash back — in the form of Gondola cash which you can apply towards future bookings. Those with Gondola status can earn up to 7% cash back as an extra rebate layered on top of an existing rewards strategy.

Plus, hotel stays booked through Gondola are treated as direct bookings with the hotel chain. This means you’ll continue to earn all of your hotel loyalty points, elite night credits, and receive your elite-status benefits — just as if you had booked directly on the hotel’s website.

Gondola will also monitor all booked stays, and if the rate drops — either in points or cash — you’ll automatically be rebooked at the lower price (as long as you're still within the no-fee cancellation policy window). This makes it easier to lock in a reservation with confidence, especially for trips where prices tend to fluctuate leading up to the stay.

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To make the platform even more rewarding, Gondola has launched a new status challenge that significantly increases the cash-back earning rate on hotel bookings through 2026. This offer can be especially valuable for travelers who expect to book multiple paid stays over the coming year.

Here are the key details:

• Book 5 nights or spend $1,500 by January 31, 2026: Earn Gondola Silver status and get an extra 5% cash back
• Book 10 nights or spend $3,000 by January 31, 2026: Earn Gondola Gold status and get an extra 7% cash back

Once you hit a new status level, the elevated cash-back rate applies to all new bookings you make through Gondola through the end of 2026 (and there are other perks in addition to the increased cash back). For frequent travelers, that extra 5–7% return can add up quickly — especially when paired with hotel points, elite bonuses, and credit card rewards.

A major perk of this challenge is its flexibility. Progress is based on bookings made by January 31, 2026 — not just stays completed by that date. So as long as you book your qualifying stay during the month of January, any future travel still counts.

Sign up for Gondola and enroll in the status challenge

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Gondola aligns with how Points Path members already think about travel optimization. Instead of spending extra time checking prices and redemption values across multiple websites, Gondola centralizes the process, while still letting you book directly with your desired hotel.

And on top of it, Gondola users can earn up to 7% cash back on all cash bookings — in addition to the points you'd normally earn with the hotel's own loyalty program and credit card points.

Gondola is designed for travelers who want convenience and maximum value from every hotel stay. If you’re planning upcoming trips — whether a short weekend stay or a full year of travel — this is a great time to explore Gondola and see how the challenge can help you earn even more from every paid night.

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