Airbnb listing: http://airbnb.com/h/athens-lake-house
The rental is in a lake community in the Catskills about 2.5 hours outside of New York City. The rental has good reviews and is priced competitively. It is currently about 35% booked (11 days so far) and is listed on both Airbnb and VRBO. Weekends usually book first and 3 out of 4 weekends are already booked. The listing would need to be booked at least 16 days for this question to resolve positively. If the remaining weekend is booked, it would bring the total to 13 days. A professional photographer also needs to come out for one of the days which would mean the rental could not be booked for that day, but the appointment has not yet been confirmed. The rental launched last month and the median lead time for bookings is about 24 days, but it has also received last-minute bookings. Not all the guests who have stayed there have left reviews.
Aug 1, 5:29pm: As of today, the first weekend in September is booked (September 2nd - 5th). I believe this somewhat decreases the odds of getting at least 16 days since it is more rare for weekdays to be booked that are not connected to a weekend and most of the days leading up to the booking are in August.
Aug 2, 9:17pm: Received an inquiry today for August 22nd - 26th (4 nights). If it gets booked, it would bring the total to 15 days and there would still be a weekend open for booking. I estimate that inquiries have an approximately 25% chance of turning into bookings, but they also show interest in a particular time period indicating that there may be demand for those days generally.
Aug 4, 8:02pm: Received a booking for August 9th - 11th (2 nights). If the 3rd weekend gets booked (I estimate this to be about 70% likely), it would take just one more day and this question would resolve as YES. I should add that this most recent booking is still within the penalty-free cancellation period, but I estimate only a 10% chance that it will cancel. Additionally, we have a tentative plan to have the photographer come on the morning of the 9th before the guests arrive.
Aug 5, 8:59pm: The photographer is confirmed for the morning of the 9th.
Aug 10, 7:40pm: The third weekend got booked today (but could still cancel penalty-free for the next ~2 days), so now we're at 15 days booked. We had to close off two "orphan" days (single unbooked days between confirmed bookings) due to scheduling conflicts with the cleaning crew, so if this most recent booking doesn't cancel, it would just take one more booking for this question to resolve as YES.
Aug 16, 5:26pm: Received another booking request today for August 22nd - 24th (2 nights), which, if it isn't cancelled (estimating 90% it will stay booked) would mean that this question will resolve as YES provided that there are no other cancellations (estimating 95% there will be no other cancellations). Additionally, there have been 3 inquiries around many of the remaining open dates where I estimate each one has an approximately 25% chance of turning into a booking.
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I missed @JonathanMann's comment of a few days ago. With only 1 more day to be booked to reach 16 days as of Aug 11, this looks likely.
@belikewater - there wasn't a cancellation, some of those days are only available for checkout. 13 days are booked.