Bookrail is the brainchild of Grant Kirkhope: it lets AI assistants like ChatGPT and Claude book independent holiday lets directly. It checks live prices and availability, takes no commission, and the owner approves every booking. It started with his own property, Rose Cottage in Fife, Scotland, believed to be the first holiday let in the UK an AI assistant can book end to end. In this ‘In Conversation With’, Grant tells us more about his own journey and how the way people are booking travel is evolving.
You were a holiday-let owner before you were a tech founder. What was the moment you decided you’d paid your last OTA commission? And how did the journey from that moment to where you are now happen?
The numbers made the case for me. I was paying commission to a booking site for guests who had already decided they wanted to stay in that part of Fife. I’ve always been interested in payments and automation, so when I saw how AI is changing booking behaviour, I rebuilt Rose Cottage’s booking journey around it. Guests get live prices, I approve each booking and the payment comes straight to me, all handled through an AI chat box. It worked on my cottage, so I turned it into Bookrail, and now I want to share the opportunity with independent owners across the UK and beyond. When that first booking went through, I realised something had changed. The playing field between independent owners and the big booking sites is levelling, and I want Bookrail to be part of that change.
For a reader who has never asked ChatGPT to book anything, explain what actually happens from their side.
You type into the chatbox what you’d say to a friend, something like “Book Rose Cottage for the first week of September, for two of us and the dog.” The assistant checks the cottage’s live calendar and prices, then comes back with the dates, the total and the deposit. You say yes and a request goes to the owner’s phone. Once they approve, which is often within minutes, you get a secure Stripe link to pay the deposit. It really is just a conversation, and much quicker than filling in forms.
Handing a booking to an AI requires a lot of trust from both guests and owners. What are the biggest misconceptions you come across?
People assume the AI is inaccurate and makes all the decisions. In fact, the owner is in control throughout. The price a guest sees is a live quote from the owner’s own calendar and rate table, the owner confirms the booking, and Stripe handles the payment straight to the owner’s bank. Bookrail’s use of AI is to connect the guest and the owner, saving time and money for both parties. Think of it as a well-briefed concierge rather than a travel agent.
Why insist the owner approves every booking? Isn’t the point of AI to take the human out of it?
I believe there should always be a human in the loop with AI, and booking a holiday let shows why. This is someone’s home, and often their livelihood. The job of AI here is to take away the admin, such as checking dates, working out prices and chasing paperwork. Deciding who stays in your house still deserves one tap from a real person, and I wouldn’t switch it on at my own cottage without it.
Your site has a section titled “What we won’t promise” and reiterates that no one can guarantee ranking in AI search. How will travellers actually discover independent properties through AI, rather than only booking ones they already know?
Right now, Bookrail works best when a guest has a place in mind. Ask ChatGPT or Claude about Rose Cottage by name and it can tell you which dates are free and what it costs; then it will send the booking request. Finding somewhere you’ve never heard of is still a work in progress, and I won’t pretend it’s a silver bullet. But I can tell you what I do know. AI is changing how people search for information, and therefore for places to stay. Clear, accurate information helps those places get discovered. Where it is, how many it sleeps, what it costs and when it’s available are the things that need to be easy to find. That’s what Bookrail helps independent owners to put in place. Nobody can promise you a ranking in AI search, and I’d be wary of anyone who does. But we give owners a strong foundation, making their properties easier to find, easier to understand and easier to book, without compromising their profits.
Is there something lost when a stay is booked by a machine? How do you keep the warmth of a host-guest relationship?
You’d be surprised. There’s more opportunity to showcase your brand with Bookrail enabled than there is with an OTA. The guest deals with the owner’s own site, the owner personally approves every request, and there’s a direct line for questions beforehand. What the AI assistant handles is the back and forth about dates and prices at eleven at night. That leaves the owner with the good parts, like the welcome message and the local tips you can’t find in a guidebook.
Your line is that Airbnb defined the app era and Bookrail is built for the AI era. What does booking a holiday look like in five years?
I think booking a holiday will become as easy as describing the trip you want to take. You might say, “A long weekend near St Andrews in May, dog-friendly, a proper fire, under £900.” An AI assistant could check availability, compare properties and offer two or three places that genuinely fit and are ready to book. And crucially, independent holiday lets could be just as easy to find and book as those listed on big platforms.
The app era rewarded whoever controlled the listing. I think the AI era will reward whoever makes their property information accurate, accessible and bookable. That’s the opportunity we’re building Bookrail around. It gives independent owners a chance to create a direct relationship with their guests.
What have you noticed about how travellers are researching and booking their stays now, compared with even a year ago?
Guests arrive better informed these days. A lot of enquiries now come with the homework already done. Today, people have access to more information than ever before, and AI assistants can provide everything from travel times to what’s open in February. When it comes to Rose Cottage, the questions I get are sharper as a result, and they tend to be about the things that aren’t on the internet.
What does this mean for boutique hotels and high-end rentals, not just cottages? Could a five-star hotel use Bookrail tomorrow?
Yes, it could. The principles are the same whether it’s a cottage or a five-star hotel. You publish live prices an AI assistant can read, you keep a person in charge of the commitment, and you take payment direct. A hotel adds room types, rate plans and a front-desk system, and Bookrail can be adapted to bring those into the booking flow. We started with holiday lets, but the ambition was always bigger. Bookrail is for independent owners who want more direct bookings and less reliance on the big platforms, and high-end rentals already fit that today. Boutique hotels are the natural next step, and I’d love to hear from hoteliers who want to help shape it.
For an independent owner or boutique hotelier reading this, what’s the single most useful piece of advice you’d give them about preparing for AI-led booking?
Start with the evidence. Ask an AI assistant what a week in June costs at your own property and whether it can be booked direct. If the answer is vague or wrong, that’s what your next guest is hearing. To fix it, bring your own website up to date with the facts and state them plainly enough for a person or a machine to read. That means location, capacity, prices, policies and how to book. Own your domain and your guest relationships, because everything else builds on that. If you want a quick read on where you stand, we’ve built a free check on the website.
What do the next 12 months look like for Bookrail?
We want more properties on board, but we’re focused on getting it right, not just growing quickly. We’re gathering momentum, starting in Scotland and building out to cover the UK. We’re developing the technology all the time to make booking direct quicker and simpler for guests and owners. We’re also opening the door beyond holiday lets, to hotels and other independent stays that want direct bookings.
You also have a cottage in Fife, Rose Cottage, that can be booked via Bookrail. Tell us more about the cottage.
Rose Cottage is an 18th-century stone cottage in Chance Inn, a hamlet nine miles from St Andrews. We kept the shell and reworked the rest. There are oak beams, a wood-burning stove, a country kitchen and a picture window framing the Fife countryside. It sleeps eight across three bedrooms and a snug, and there’s a mezzanine with a projector and games consoles that children tend to claim. It has an EPC A rating, which is rare for a building of its age, and it runs on solar panels, battery storage and a heat pump, with a charger for the car. Dogs are welcome too. There’s plenty to discover nearby, from coastal and country walks and pretty fishing villages to castles, independent cafés and traditional pubs.
For readers considering visiting, please tell us what your perfect weekend in Fife looks like.
Arrive on Friday, light the stove and pour a glass of wine. Saturday would start in St Andrews with a walk on West Sands, the cathedral ruins and a look at the Old Course, then a long lunch in town. In the afternoon I’d head along the East Neuk through Crail and Pittenweem and finish with fish and chips on the harbour at Anstruther. Sunday would be Tentsmuir forest and beach, then back to the cottage for a film on the mezzanine.
Luxury is highly subjective; what does it mean to you personally?
For me it’s mostly about time. It’s a few days where nothing is rushed and nobody needs anything from you, somewhere warm, quiet and well looked after, where the small things have been thought about before you arrive. It’s also knowing there’s a real person behind it who cares whether you enjoyed your stay.
Finally, what is your life motto? (if you have one).
Build it for yourself first. That’s how Bookrail started.
