First let me say that I would change the design of the "Booking" table. It is designed on the order of a spreadsheet.
Lets say John wanted to rent a backhoe next Tuesday for 3 days. So you create a record and set the status to Booked.
Where do you enter the date booked: the Checked Out field or the Checked in field?
I would have one date field: "EntryDate".
So at the end, there would be 3 records:
STATUS________Entry Date
----------------------------
Booked ________ 2/2/2016
Checked Out____ 2/9/2016
Checked In______2/12/2016
I also added a table for statuses. Easier than calculating in the query. And easier if you wanted to add "Out of service" and "Returned to service".
Look at Query2. It is based on Query1. (Catchy names - yes???
)
Is that what you want?