How to drop column with constraint?

First you should drop the problematic DEFAULT constraint, after that you can drop the column

alter table tbloffers drop constraint [ConstraintName]
go

alter table tbloffers drop column checkin

But the error may appear from other reasons – for example the user defined function or view with SCHEMABINDING option set for them.

UPD:
Completely automated dropping of constraints script:

DECLARE @sql NVARCHAR(MAX)
WHILE 1=1
BEGIN
    SELECT TOP 1 @sql = N'alter table tbloffers drop constraint ['+dc.NAME+N']'
    from sys.default_constraints dc
    JOIN sys.columns c
        ON c.default_object_id = dc.object_id
    WHERE 
        dc.parent_object_id = OBJECT_ID('tbloffers')
    AND c.name = N'checkin'
    IF @@ROWCOUNT = 0 BREAK
    EXEC (@sql)
END

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