Connor Reed, 19, and 20-year-old Aragorn Dudley both wrote to a judge stating how sorry they were and vowing to reform.
Reed, of Albert Manor, Britton Street, Gillingham, pleaded for a chance to receive drug rehabilitation treatment.
“I can get back on the straight and narrow and stay off drugs,” he wrote.
But he and Dudley, of Albert Road, Gillingham, were each jailed for 22 months after they admitted one burglary and asked for others to be considered.
Matthew Turner, prosecuting, said the pair broke into a house in Crescent Gardens, Swanley, on September 7 this year and stole war medals and other property.
Police officers found Dudley hiding in a ground floor toilet. Reed was arrested nearby. All the property was recovered.
The pair both admitted also burgling a house in Meopham. Reed further admitted break-ins in Balmoral Road and Britton Street, Gillingham, and Dudley two in Andover, Hampshire.
They both had previous convictions for burglary, Mr Turner told Maidstone Crown Court.
Robert De Banzie, defending, said both Reed and Dudley wanted to change and had written heartfelt letters.
Urging that Reed be given the chance to beat his addiction, Mr De Banzie said: “Until that circle is broken we will be here time and time again.”
But Judge Charles Byers said both Reed and Dudley had previously been given community orders and they had not worked.
“There comes a time when one has to look to what is right for the public as well as what is right for the defendant,” he said.
“They will get help in custody.”
Passing sentence, he said: “Burglary is one of the most horrible crimes because the public are rightly concerned at the level of it.
"It causes misery to those who come across the scene afterwards.
“Some times that stays with them for the rest of their lives and they are deprived of property they have worked hard to achieve.”
The judge added: “I appreciate both of you have had particular troubles, but you have both led thoroughly dishonest lives.”