Artificial intelligence appears set to play a decisive role in the short-term rental property market—particularly in accommodation search. Traditional holiday searches based on filters, checkboxes and endless scrolling seem to be reaching their limits.
The UK-based Forge Holiday Group, which owns well-known brands such as Sykes Cottages and Forest Holidays, is already testing a new model: an AI-powered digital concierge that “understands” what travellers want when they speak naturally.
The new AI assistant is called Connie the Concierge and, according to the group’s CEO Graham Donoghue, it has been designed to allow users to search for and plan holidays using simple natural language. Instead of applying dozens of filters, travellers can simply say or type:
“I’m looking for a quiet seaside cottage that’s pet-friendly.”
From filters… to conversation
Connie is being developed in collaboration with Microsoft and UK data consultancy Dufrain, leveraging conversational AI and machine learning. The system is trained on Forge’s internal data, including guest preferences, property features and booking history.
The goal is to move away from mechanical, tiring searches towards a more intuitive and human experience—one that resembles a conversation with an experienced travel advisor.
For now, Connie is in an internal testing phase and is not yet available to the public. However, Forge’s bet is clear: the future of travel search and discovery will be AI-powered, conversational and deeply personalised.
Forge Holiday Group manages more than 30,000 properties and serves over three million guests annually. Its portfolio includes holiday homes, cabins, lodges, caravans and tourist accommodation in the UK and internationally, including Bachcare in New Zealand.
Not the first step but a step further
The market has already begun to experiment. In 2024, Landfolk introduced Daisy, a visual search tool based on “mood” and terms such as “seaside escape” or “forest hideaway”. Airbnb is also moving in similar directions.
What sets Connie apart is that it combines real-time conversation with internal data, raising the bar for what it means for a listing to be truly “search-ready”.
A quiet message to owners and property managers
This development sends a clear—albeit still informal—message to property managers and owners: listings with vague titles, poor descriptions or incomplete amenity information risk being “lost” within AI-driven search systems.
While platforms do not yet penalise such content, tools like Connie clearly indicate where the market is heading and what will soon be required for a property to remain visible.
In this new landscape, solutions such as Listing Optimizers (like those offered by PriceLabs) may become critical, helping owners identify gaps in titles, descriptions and amenities before these translate into lost visibility and bookings.
Holiday search is not changing loudly. It is changing quietly—and it now speaks our language.
Would you like to learn how to grow your short-term rental business by leveraging technology and emerging market trends? The Short Stay Athens Conference, on February 19–20, 2026, brings together the people and the data shaping the future of the industry.
Tip: Don’t miss the presentation by Alexandros Karavitis, CEO of Hosthub, titled “The Past, Present and Future of AI in Short-Term Rentals.”
