How do I create a multi-day booking?

A wedding weekend with a Friday rehearsal and a Saturday reception. A three day festival. A week long rental. Check Cherry handles all of these on a single booking by letting you add multiple packages to it, each with its own date and time.

Adding Multiple Packages to a Booking

This is the easiest way to cover multiple dates, and it is where most people should start. Each package carries its own date and time and becomes its own line item on the invoice, so the client sees one clean booking with all their services and you see the whole job in one place.

When you are creating a new proposal or booking, click Add Package to add the next one. On a proposal or booking that already exists, the button reads Add Another Package and sits below the packages already on it.

This works well when:

  • A client needs the same service on two or more separate dates
  • A wedding weekend has a rehearsal dinner on Friday and a reception on Saturday
  • A multi-day corporate event needs different services each day
  • Two packages start at different times on the same day, like ceremony and reception coverage

Letting Clients Add Multiple Packages Online

If you offer online booking, you can let clients do this for themselves during checkout. It is off by default.

ManageBooking EngineGeneral
Go to General.
Scroll to the Multiple Packages card.
Under When booking online, allow the customer to, choose Add additional packages with multiple dates & times.
Click Save.

Once that is on, a client who has selected their first package sees an option to add another. A banner at the top of the screen reminds them they are adding to their current booking, and they can keep adding as many packages as they need.

If multi-date work is rare for you, it is fine to leave this off. It adds a decision to checkout, and you can always add the second package yourself after the client books.

Daily Rate Packages

Most packages are priced by the hour and cover a single date. Check Cherry also supports all day packages priced by the day. Set the package to Date Only and the client picks a date, or a range of dates, with no time selection. The booking blocks the whole day.

This is the better fit when you regularly rent for more than a couple of days and quoting it hour by hour makes no sense.

ManagePackages
Go to Packages and click Add a Package, or open an existing package.
Give it a title and description. Something like "Open Air: Multi-Day Coverage".
Open the Pricing & Scheduling tab.
Under Scheduling Mode, choose Date Only and click Save.
In the Pricing section, enter your Starting Rate and the Number of days included in it. Usually one.
Set Allow customer to book extra days to Yes, then enter your Daily Rate along with a Minimum length and Maximum length in days.
Click Save.
Switching a package to Date Only clears its extra hours pricing, and switching back clears the extra days pricing. Set your pricing after you switch, not before.

Once the package exists, there are two ways it gets used:

  • When you build a proposal or booking with it, enter the number of days and Check Cherry prices it off your daily rate.
  • If the package is public, clients can choose it during online booking and enter the number of days themselves.

Two Ways to Cover Multiple Days

Use one Date Only package for consecutive days. Best for continuous coverage like a 3 day festival or a weekend retreat. The client picks a start date and Check Cherry fills in the rest of the range. See how to create a multi-day package.

Use one package per date. Best when the dates are not consecutive, or the service changes from day to day. A rehearsal dinner on Friday and a reception on Saturday is a good example.

You can mix the two formats on one booking. Use Date & Time for days that need a start time, and Date Only for days that don't.

What Changes on a Date Only Booking

  • No start or end time shows on the booking, invoice, or proposal.
  • The whole day is blocked in availability checks. A multi day package blocks every day in the range.
  • It syncs to Google Calendar as an all day event.
  • Time tokens in automated messages come out blank. Date tokens still work.
  • Days you have marked available for only certain hours still accept Date Only bookings. Only fully closed days block them.
  • Staff arrival times work as usual. Set them per staff member.
If any package on a booking is a multi day Date Only package, the proposal shows date ranges for every package on that booking.

Location Limitations

Each booking can only have one official location in order to keep tax and travel calculations simple. If the client needs multiple venues, you can create separate bookings or you can add the additional addresses to the package details and calculate tax and travel manually

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Last updated August 19, 2026 11:43