A late answer
If your are using SQLITE version 3.7.11 or above, then multiple rows insert is possible by this syntax,
SIMPLEST WAY
INSERT INTO Rating (rID, mID, stars, ratingDate) VALUES ('207', '102', '5', null) , ('207', '102', '5', null) , ('207', '102', '5', null)
The above clause posted in question do work if the new SQLITE version is used.
SELECT CLAUSE
insert into Rating
SELECT '207' AS rID, '101' AS mID, '5' AS stars, null AS ratingDate
UNION SELECT '207', '102', '5', null
UNION SELECT '207', '103', '5', null
UNION SELECT '207', '104', '5', null
UNION SELECT '207', '105', '5', null
UNION SELECT '207', '106', '5', null
UNION SELECT '207', '107', '5', null
UNION SELECT '207', '108', '5', null
or SQL is
insert into Rating (rID, mID, stars, ratingDate)
SELECT '207', '101', '5', null
UNION SELECT '207', '102', '5', null
UNION SELECT '207', '103', '5', null
UNION SELECT '207', '104', '5', null
UNION SELECT '207', '105', '5', null
UNION SELECT '207', '106', '5', null
UNION SELECT '207', '107', '5', null
UNION SELECT '207', '108', '5', null
REMEMBER I you do not want to check for duplicate in above set of inserted values then use UNION ALL
in place of UNION
as it will be little faster.