Booking's $100 Million Plan

Booking Holdings said it plans to make a $100 million investment in an internal AI startup, Vayo. That’s a lot of money for an unproven startup geared to organize, monitor and potentially book a trip on a Booking brand or Expedia, and one that’s just debuted a private beta.

Well, plans can indeed change and Booking seemingly hasn’t committed the $100 million to Vayo just yet.

It seems like a smart move for Booking to spread AI bets among its two new internal startups, including the Steve Hafner and Paul English-run Lola, as well as Priceline, Agoda and Booking.com.

But in an era of employee downsizing at Booking and when the various brands compete for scarce resources, that $100 million figure must be turning heads.

Skift Aviation Forum · NYC · November 11-12

Planes are full. The profit math isn’t. Delta just swallowed $6B in fuel and cut its outlook while revenue rose 16%. On November 12 at the TWA Hotel, JFK, the leaders who turn record traffic into real margin take the room.

IAG, Breeze Airways, and Air Canada lead a 2026 lineup before 300+ senior aviation leaders.

What Travel Can Learn From Turo

Headlines

Why Everyone Wants to Give You 10% Back on a Hotel

October 14, 2026

Ten percent back has become a common hotel reward, and what a company can afford to pay depends on what the customer is worth to it after checkout.

Booking Holdings Plans to Fund New AI Startup Vayo With $100 Million

October 14, 2026

Booking already has tools that organize trips. Vayo's proposition is that AI can turn the itinerary into something more: a system that learns how you travel, watches the entire trip, and starts working before you ask.

Fighting Spirit’s Data Sale to Google: Court Filings Show the List Getting Longer

October 12, 2026

The deal has faced months of delays and pushback, coming to represent a thorny issue of how far bankruptcy code should go to protect employee privacy as AI makes rapid advances.

India Is Now Skyscanner’s Biggest Market, and Nearly Half Its Searches Go Abroad

October 12, 2026

Indians aren’t going to book a trip just because you’ve been selling them the destination. They want to see the value first.

Travel AI’s Prove-It Phase, Visibility, and the Booking Gap

October 11, 2026

Skift's Data + AI Summit in Europe this week just showed that AI may be changing travel distribution and internal operations, but booking volume is another story.

Vrbo Faces Blowback on Rising Commissions, Plans to Ease Rate Parity Rule

October 7, 2026

From a competition perspective, Vrbo is catching up to Booking.com and Airbnb in pushing the fee burden onto hosts. Eliminating or greatly reducing guest fees has great optics, but travelers will end up paying for them in the form of higher rates.

SUBSCRIBE TO VERY ONLINE

Watch or Listen

Brian Chesky commits to launching Airbnb's AI travel agent in 2027 and bets the chat interface is the wrong format for travel, Barry Diller walks away from an $18 billion MGM deal but leaves the door open, and two of travel's biggest investors reveal they're putting their money into things AI can't copy.

On today's Skift Daily Briefing, Sarah Dandashy breaks down why Airbnb is building its own front door instead of joining ChatGPT, what Diller's MGM withdrawal says about the timing of big Strip consolidation bets, and why the smartest travel investors are chasing land, wellness, and high-speed trains in an AI-commoditized world.

GET THE FULL EPISODE

Skift Travel 200

How are public travel tech companies performing around the world? The Skift Travel 200 pulls the data you need to know to understand the market. Paid subscribers get full access here.

SEE THE ST 200 →