hoteltech.news September 30, 2026
Artificial Intelligence1 min read

Kayak founders return with Lola, backed by Booking Holdings

Voice reading · ~1 min

Two decades after launching Kayak to sort out the chaos of finding flights and hotels online, Steve Hafner and Paul English are back with a new bet. It is called Lola, and it arrives backed by Booking Holdings to try out a fresh way of selling travel for the AI era, according to Smart Travel News.

The pattern repeats, only the tools change. Where Kayak once organised abundance through a metasearch that compared and ranked options for travelers, Lola works the conversational angle. An AI agent that helps decide and book, rather than just showing a list. Booking's involvement is the detail worth watching: the group is testing a model that could end up shaping how hotel direct sales get done.

My read: this is good news for the industry. Hafner and English have a track record, Booking has the muscle, and AI agents open a door that hotels should not ignore.

If the big test works, independent hotels could gain another channel to push direct bookings and cut some friction for travelers. Worth keeping an eye on.

Quick questions

Who are the founders behind Lola and Booking Holdings' new AI play?
Steve Hafner and Paul English, the founders of Kayak, are back with Lola, a new travel venture backed by Booking Holdings to test how AI agents sell trips.
What is Lola and how does it fit into Booking Holdings' strategy?
Lola is the new venture from Kayak's founders focused on selling travel in the AI era. Booking Holdings is backing it as a test bed for a conversational way to book, away from the traditional metasearch model.
Why does Booking Holdings backing Lola matter for hotel distribution?
Because Booking controls a huge share of online travel demand. If its AI agent format works, it could reshape how travelers discover and book hotels, including direct sales for independents.
How does the Lola model differ from what Kayak did 20 years ago?
Kayak organised travel search by comparing and ranking options. Lola leans on AI agents to guide the traveler through the decision itself, not just hand over a comparison list.
Should independent hotels pay attention to Lola's launch?
Yes. A new AI-driven booking channel backed by Booking Holdings could open another route to direct demand. Worth testing early, before the model is fully proven.

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