The midnight scroll through hotel listings just got a digital makeover. Instead of scrolling through endless listings, you simply type your request like you’re texting a well-traveled friend. That’s the promise behind Hotels.com‘s latest gambit—an AI chatbot that’s part digital concierge, part overeager intern.
Launched in May 2025 as part of a comprehensive brand overhaul, the chatbot arrives alongside a redesigned app interface and a new mascot named Bellboy. The timing isn’t coincidental—Hotels.com has been fighting to regain ground in an increasingly competitive landscape where competitors like Booking.com have been refining their AI Trip Planner since June 2023, now available across multiple markets with features like Smart Filter and property-specific Q&A capabilities.
The Great AI Travel Race
Hotels.com joins a growing field of travel platforms betting on conversational AI to capture wandering minds. Booking.com’s recent expansion of Smart Filter tools lets users describe properties in natural language—”Hotels in Amsterdam with a great gym, a rooftop bar, and canal views”—with GenAI scanning entire inventories to deliver tailored results.
This isn’t just about keeping up with the Joneses. According to Booking.com’s CTO Rob Francis, more than half of travelers surveyed are now willing to accept AI recommendations, a significant shift from when their AI trip planner first launched. The question isn’t whether AI will reshape travel booking—it’s who will do it best.
When Technology Meets Wanderlust
Hotels.com’s chatbot shines in its natural language processing. Users can make requests like “rooftop bar hotel in downtown Portland” or “pet-friendly place near the beach,” or even ask for suggestions on the best vacation spots for their next getaway and the system translates these conversational queries into filtered results. Early data suggests this approach resonates—Expedia Group reports a 35% increase in booking conversions among users engaging with the smart filter feature.
But here’s where the magic meets reality: the chatbot occasionally suggests Manhattan hotels for Brooklyn searches, like a GPS that’s had one too many espressos. These accuracy hiccups reveal the technology’s growing pains, reminding us that even artificial intelligence can get lost in New York City.
The booking process itself remains refreshingly straightforward. Selected dates carry over seamlessly to the reservation page, and users can complete transactions without leaving the app. It’s the kind of streamlined experience that makes you wonder why booking travel ever felt complicated.
The Gaps in Digital Hospitality
Despite its conversational charm, the chatbot’s limitations become apparent when travelers seek comprehensive trip planning. Flight bookings remain off-limits, and while the system can suggest restaurants and attractions, it doesn’t provide booking links or integrate recommendations into itineraries.
Compare this to Booking.com’s more mature AI ecosystem, which includes property-specific Q&A features that can answer questions like “Are there charging stations for electric vehicles onsite?” by scanning property listings, reviews, and photos. Hotels.com’s approach feels more like a specialized tool than a complete travel companion.
The trip management feature reflects similar constraints. Hotels appear automatically in saved itineraries, but flights and experiences require manual entry through notes—a workflow that feels more like digital housekeeping than seamless planning.
