Holidaymaker says Booking.com's AI chat confirmed a host's bank-transfer request before his Positano villa booking proved a scam
A British customer who booked a five-day villa stay in Positano, Italy, through Booking.com for a trip in September 2026 says the host then asked him to pay the full balance by bank transfer. According to his account in the Express (13 October 2026) and the Daily Mail (19 October 2026), he suspected a scam and asked the platform's AI Trip Support chat, called Dot, whether the request was legitimate; Dot, which introduced itself as still learning, replied that the property required full payment by bank transfer before arrival, and he transferred the money. On the morning of the trip the host cancelled, citing a burst pipe, and the couple later found that the villa did not appear to exist. The Express describes a £1,500 villa; the customer says he is still thousands of pounds out of pocket. Booking.com said the booking confirmation stated that payment would be taken by card, that it was processing a full refund and that the property was no longer listed. The chatbot exchange rests on the customer's account; Booking.com's quoted statement does not address it.
- AI system
- Booking.com AI Trip Support (reported)
- Occurred
- Sept 2026
- Reported
- 13 October 2026
- Event location
- Unknown
- What the AI did
- Communicated with the person
- Reported harm
- Financial LossPsychological Distress
- Whose AI use
- An institution’s AI use
- Setting
- Finance · Everyday life
- Evidence
- AI involvement reported · Causal attribution alleged · 2 sources, 1 underlying account
- 6 claims: 6 reported. 5 open questions
- People reported harmed
- 1 person
AI system as recorded: Booking.com's AI Trip Support chat, called Dot, which the customer asked whether a host's request for payment by bank transfer was legitimate (as the customer describes the exchange to the press)
What Happened
The request. The customer booked a private villa in Positano through Booking.com for a five-day trip in September 2026. Before the trip, he says, the host messaged him asking for the full balance by bank transfer. Suspecting a scam, he asked the platform's AI Trip Support chat, Dot, whether this was correct.
The chatbot's reply. According to both articles, Dot introduced itself as still learning and replied: "Yes, the property requires full payment via bank transfer before your arrival." Reassured, he transferred the money.
The cancellation. About an hour before the couple left for the airport, the host emailed to say it could no longer host them because of a burst water pipe. He then concluded it was a scam. He says Booking.com agreed to pay for alternative accommodation, and Booking.com says the trip began the same day as planned. In Positano they could not find the villa, and a restaurant owner opposite its supposed location told them someone had come a month earlier with the same photographs.
The platform's response. Booking.com said the booking confirmation explained that payment would be taken by card rather than by bank transfer, that it was processing a full refund and that the property had been removed. Its statement does not mention the chatbot. The couple's separately delayed luggage on the outbound flight is unrelated to the chatbot and is not part of this record.
Reported harm
The customer says Booking.com's AI chat confirmed a fraudulent host's request for payment by bank transfer, after which he transferred the money for a villa that did not exist; he describes the experience as absolutely horrendous and one of the most stressful things anyone could go through, and Booking.com says it is refunding him.
Outcome
OngoingBooking.com told both outlets it was processing a full refund, that the property was no longer listed and that it had helped the customer on the day of the cancellation; the customer says he is still thousands of pounds out of pocket and is asking only for his money back, not for compensation. No complaint, regulator or court action is reported.
What remains unknown
- The exact amount transferred (the Express describes a £1,500 villa; the customer says thousands of pounds).
- Whether Booking.com has paid the refund it said it was processing.
- The date of the chatbot exchange and the transfer, beyond being before the September 2026 trip.
- Whether Booking.com has reviewed the chatbot's reply; its statement does not mention the chatbot.
- The chatbot's underlying technology.
What the evidence supports
AI involvement: reported. Both articles quote the reply the customer says Booking.com's AI Trip Support chat, Dot, gave when he asked whether the host's bank-transfer request was correct: that the property required full payment via bank transfer before arrival. He says he transferred the money because of that reply, and the listing turned out to be fraudulent. The exchange rests on his account; Booking.com's quoted statement neither confirms nor disputes it, and no transcript is published.
6 claims: 6 reported. What the statuses mean
Reported The customer booked a private villa in Positano, Italy, through Booking.com for a five-day trip in September 2026, and before the trip received a message from the host asking him to pay the full balance by bank transfer.
Causal attribution. Customer account relayed by two outlets in one chain.
- express.co.uk(opens in new tab) supports · English
booked a romantic five-day trip to Positano, Italy ... last month [September 3]. Before the trip, ... says he received a message from their villa host saying he needed to make a bank transfer for the full balance.
- dailymail.com(opens in new tab) supports · English
booked a villa via Booking.com for five days, and prior to the trip, claims he received a message from the host saying he needed to transfer the full balance over.
Reported Suspecting a scam, the customer asked Booking.com's AI Trip Support chat, Dot, whether the request was correct, and Dot, which introduced itself as still learning, replied that the property required full payment via bank transfer before arrival.
Causal attribution. The chatbot's reply is quoted from the customer's account; no transcript or platform confirmation is published.
- express.co.uk(opens in new tab) supports · English
decided to check with Booking.com's AI Trip Support chat 'Dot' and asked if this was correct. ... Dot, which introduced itself as "still learning", replied: "Yes, the property requires full payment via bank transfer before your arrival."
- dailymail.com(opens in new tab) supports · English
Dot, which introduced itself as 'still learning', confirmed: 'Yes, the property requires full payment via bank transfer before your arrival.'
Reported Reassured by the reply, the customer transferred the money; on the morning of the trip the host said it could not host the couple because of a burst pipe.
Causal attribution. The customer attributes his decision to transfer the money to the chatbot's confirmation.
- express.co.uk(opens in new tab) supports · English
Reassured it was legitimate ... transferred the cash over only to receive a message on the morning of the trip claiming the property was flooded from a burst pipe
- dailymail.com(opens in new tab) supports · English
As such, the holidaymaker went ahead and transferred the money. ... However on the morning of the trip, he received a message from the host claiming that a burst pipe had caused the property to flood
Reported In Positano the couple could not find the villa, and a restaurant owner opposite its supposed location told them someone had come a month earlier with the same photographs.
Causal attribution. Customer account.
- express.co.uk(opens in new tab) supports · English
We actually tried to find the accommodation because we were staying in Positano and it doesn't exist.
- dailymail.com(opens in new tab) supports · English
'We showed him pictures and he said to us "someone was here a month ago with the exact same photos in your same situation".'
Reported The Express describes the villa as costing £1,500, and the customer says he is still thousands of pounds out of pocket and described the experience as absolutely horrendous and one of the most stressful things anyone could go through.
Causal attribution. The customer's own description of the loss; the amounts are not reconciled in either article.
- express.co.uk(opens in new tab) supports · English
his £1,500 villa turned out to be a "scam" - that Booking.com backed. ... It was absolutely horrendous and one of the most stressful things you could ever go through.
- dailymail.com(opens in new tab) supports · English
'It's not a couple hundred quid, it's thousands and thousands of pounds that they owe me not because of any fault of my own.'
Reported Booking.com said the booking confirmation explained that payment would be taken by card rather than by bank transfer, that it was processing a full refund and that the property was no longer listed; its statement does not mention the chatbot.
Causal attribution. The platform's statement as quoted by both outlets; it neither confirms nor disputes the chatbot exchange.
- express.co.uk(opens in new tab) supports · English
In this case, the confirmation explained that payment would be taken by card rather than by bank transfer. We can confirm that we are processing a full refund, and the property is no longer listed on our platform.
- dailymail.com(opens in new tab) supports · English
'We can confirm that we are processing a full refund, and the property is no longer listed on our platform.'
Sources
2 sources inspected, from 1 underlying account. Sources that repeat one account do not corroborate each other.
- Express, 13 October 2026: 'I was scammed £1,500 through a popular travel website - it could happen to anyone'(opens in new tab)
s1 · express.co.uk · News · English · Inspected · 13 October 2026 · Shares an underlying account with another listed source · Primary
- Daily Mail, 19 October 2026: Husband-to-be loses thousands after Booking.com AI chatbot tells him to pay holiday scammer(opens in new tab)
s2 · dailymail.com · News · English · Inspected · Shares an underlying account with another listed source
How the sources were read, and where the events happened
Read in English on 2026-10-20 through a Wayback Machine capture of the Express page (the live page returned HTTP 202 with no body). The article and the Daily Mail piece carry the same quotations from the customer and the same Booking.com statement, so they are treated as one reporting chain. Applies to s1.
Read in English on 2026-10-20 from the Daily Mail page (full text). Published six days after the Express article with the same quotations; treated as part of the same chain. Applies to s2.
Event countries: Unknown. Affected-person countries: United Kingdom. Court countries: Unknown.
The articles describe the customer as British and from south-east London. The fraudulent listing was for a villa in Positano, Italy, but neither article says where he was when he used the chat or made the transfer, so no event country is recorded.
Reviewed for publication 2026-10-20: Published as a concrete adverse experience with a travel platform's AI customer chat: the customer says the chat told him a host's request for payment by bank transfer was correct, he paid, and the listing proved fraudulent; the platform says it is refunding him. The chatbot exchange is attributed to the customer throughout.
People described
A British adult customer of Booking.com who asked its AI chat about a host's payment request before a trip to Italy
People reported harmed in this case
1 person
1 AI participant · 0 other people harmed
One person: the customer who asked the chatbot about the host's payment request and then transferred the money. His partner travelled with him, but the articles do not report a loss of hers that followed from the chatbot's reply, so she is not counted.
Counted once within this case. The same person may appear in other cases. This count does not establish AI causation.
Cite this case
Compiled per our published methodology: verification statuses, sourcing standards, and corrections process.
APA
NOPE. (2026). Holidaymaker says Booking.com's AI chat confirmed a host's bank-transfer request before his Positano villa booking proved a scam. AI incidents. https://nope.net/incidents/2026-holidaymaker-says-booking-com-ai-chat-confirmed-hosts-bank-transfer-request-before-villa-booking-proved-a-scam
BibTeX
@misc{2026_holidaymaker_says_booking_com_ai_chat_confirmed_hosts_bank_transfer_request_before_villa_booking_proved_a_scam,
title = {Holidaymaker says Booking.com's AI chat confirmed a host's bank-transfer request before his Positano villa booking proved a scam},
author = {NOPE},
year = {2026},
howpublished = {AI incidents},
url = {https://nope.net/incidents/2026-holidaymaker-says-booking-com-ai-chat-confirmed-hosts-bank-transfer-request-before-villa-booking-proved-a-scam}
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