• WITH DistinctDays AS (

    SELECT DISTINCT ID, ReadingdateDT = CAST(CAST(Readingdate AS DATE) AS DATETIME)

    FROM #tempreadings

    )

    SELECT *

    FROM DistinctDays d

    CROSS APPLY (

    SELECT Timeslot = DATEADD(minute,n*30,ReadingdateDT)

    FROM (VALUES

    (0),(1),(2),(3),(4),(5),(6),(7),(8),(9),

    (10),(11),(12),(13),(14),(15),(16),(17),(18),(19),

    (20),(21),(22),(23),(24),(25),(26),(27),(28),(29),

    (30),(31),(32),(33),(34),(35),(36),(37),(38),(39),

    (40),(41),(42),(43),(44),(45),(46),(47)

    ) iTally (n)

    ) x

    CROSS APPLY (

    SELECT TOP 1 *

    FROM #tempreadings i

    WHERE i.ID = d.ID

    AND Readingdate >= Timeslot AND Readingdate < DATEADD(minute,30,Timeslot)

    ORDER BY Readingdate DESC

    ) y

    “Write the query the simplest way. If through testing it becomes clear that the performance is inadequate, consider alternative query forms.” - Gail Shaw

    For fast, accurate and documented assistance in answering your questions, please read this article.
    Understanding and using APPLY, (I) and (II) Paul White
    Hidden RBAR: Triangular Joins / The "Numbers" or "Tally" Table: What it is and how it replaces a loop Jeff Moden