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I'm asking specifically about Hilton properties, but you can answer generally too. Once I check in to a hotel room online or in the hotel app, can I still cancel my reservation, for instance, if my flight is delayed as long as I'm within the hotel's cancellation window (often 6PM same day)?

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    I don't know the actual answer (for Hilton) hence a comment. I would wonder that you would even think it possible to cancel your reservation, once you've checked in. I see no difference whether you check in to your room virtually or in person, you've accepted the room as is and agreed to pay for it, at least for a single day rate. The hotel has accepted your check in, and now flags the room unavailable and occupied. – CGCampbell Jan 2 '16 at 19:03
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    @CGCampbell Hilton allows you to check-in the day before arriving, so the act of checking in online doesn't directly flag the room as occupied. – Doc Jan 2 '16 at 19:42
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    This depends on many factors, including when you made the reservation and when you are wanting to cancel it. It may also depend on how you paid, which room (or rooms) you reserved, preferred customer status, whether you booked directly, through an OTA, or through a traditional travel agency, and other factors. When you consider other chains, too, the possibilities are literally endless. The only possible general answer is "check your reservation cancellation policy." – Flimzy Jan 2 '16 at 22:54
  • The accepted answer is the one I was looking for. I booked a hotel the most general way: through the Hilton website with a refundable rate (6pm cancellation date). The question was about whether checking in invalidates the 6pm cutoff. – Wesley Bland Jan 2 '16 at 23:31
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Firstly, note that most Hilton properties now have a "day before arrival" cancellation policy on most reservations. Some corporate rates override this and still have a 4pm/6pm/etc policy.

However if you are still before the cancellation time on your reservation then you can still cancel even if you have checked in online - however you will need to contact the hotel directly to do so.

The Digital Check-in FAQ covers this to some extent where it says "Should you need to cancel a reservation, please call the hotel directly. We plan to enable in-app cancellation in the near future."

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To answer generally, there is the official policy, and then there is what the hotel chain or individual hotels do in practice. If it is before the cancellation deadline, then officially you are permitted to cancel. If it is past the cancellation deadline, then you need to contact the hotel chain guest assistance desk or the individual hotel directly, and plead your case. If you have a pre-paid, non-refundable rate, it's more difficult, but sometimes an exception is made. If you need to cancel because your flight is delayed or a similar circumstance out of your control, you may be permitted to do so. If you ask to have your reservation shifted to be a day later instead of cancelled, that's often easier for a hotel to do. In my own experience, I've always been permitted to shift or cancel when a flight delay or bad weather caused the issue.

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