The 'Mean Girls' actress offered staged pictures of her with mother Dina, sister Ali, her brothers and boyfriend Riley Giles celebrating the holidays to several celebrity magazines.
She initially demanded a six-figure sum, but eventually dropped the price to $20,000 when she failed to find a buyer.
A source told MSNBC, "She thinks she's a huge star. She thinks everyone is dying to read about her, but she's lost her fan base. Her decisions are being driven by cash, not repairing her image."
Lindsay, 21, reportedly failed to sell the pictures, but made some money from her family shopping trip to New York's Armani Exchange and Intermix store on November 23.
It is claimed Lindsay tipped off the paparazzi she would be there and was paid to visit the clothing store.
The source added, "It seems like everything Lindsay does is to make money."
Last month, it was claimed the troubled star - who completed treatment in rehab for drug and alcohol addiction and served a prison sentence for driving under the influence - is broke after blowing her $7 million fortune on drugs and partying.