Deep navy editorial illustration of two colossal corporate structures stretching across a harbor, each lowering a glowing mechanical arm toward a small independent hotel facade standing alone between them

The OTA AI Counterattack: Booking and Expedia Are Buying Their Way Into the AI Booking Layer

The short answer The OTAs are not being disintermediated by AI travel planners. They are buying and building their way into owning the AI booking layer instead. Expedia Group acquired Layla, the Berlin-based conversational AI trip planner, in July 2026 (Skift, July 31, 2026). Booking Holdings is running at least five consumer-facing AI experiments, with Priceline’s revamped agentic assistant Penny cited by executives as the standout early performer on satisfaction, engagement and conversion (Skift, September 14, 2026). OpenAI, after testing direct transactions, stepped back in March 2026 and refocused ChatGPT on discovery — routing live pricing and checkout through partner apps, starting with Expedia and Booking.com. And Google’s AI Mode hotel booking launched on August 27, 2026 with ten partners: five chains, and five OTAs. ...

September 16, 2026 · 9 min · Palmtree.ai