Booking Holdings Launches Lola, a Standalone AI Travel Assistant From Kayak's Founders

Booking Holdings is betting that a single AI assistant built from scratch, with a membership model and human concierge service, can hold together a trip that its existing apps handle separately.

On September 29, 2026, the company introduced Lola, an AI assistant designed to work as a standalone online travel agency rather than a feature inside Booking.com. It was created by Kayak co-founders Steve Hafner and Paul English and operates as a wholly-owned Booking Holdings subsidiary. Hafner reports directly to CEO Glenn Fogel and was given a "greenfield" mandate. The team of roughly 20 people, based in New York and Cambridge, Massachusetts, spent five months building it.

Membership instead of commission

• Free tier, ad-supported
• Plus: $5 a month, 12-month commitment
• VIP: $25 a month, 12-month commitment

A sample comparison prices a four-night Miami Beach stay at $783 for VIP members versus $997 on Booking.com and Expedia. Leadership expects about 90% of active users to stay on the free tier.

Supply and partners

Lola draws on inventory from Booking Holdings brands and outside partners including OpenTable, ResX, SeatGeek, GetYourGuide and FareHarbor. Ten Group provides concierge services and has enhanced-benefit relationships with roughly 5,500 to 6,000 hotels.

Hafner said: "At Lola, we're solving for what should I do this weekend," distinguishing it from Kayak's flight-focused approach.