Nathan Collinson, 33, was stood outside a house on a named street in Scarborough when he shouted the two girls over as they passed by, York Crown Court heard.
He touched one of them intimately and kissed both victims, said prosecutor Rob Stephenson.
Collinson was arrested after being identified on CCTV and bailed, but the brazen criminal then burgled a guest room at the Grand Hotel in Scarborough – while the occupiers were asleep.
The sexual offences occurred at night in October 2020 when the two girls were “shouted (over) by (Collinson) who was stood outside an address on (the named street)”, said Mr Stephenson.
“The (victims) both approached him and he kissed each of them,” added the prosecutor.
Collinson touched one of them on an intimate area over her clothing and kissed her again.
He then kissed the other girl and walked with both victims to the corner of the street where there was “more kissing and hugging and embracing”.
“Everything was captured on CCTV,” said Mr Stephenson.
The girls eventually walked away but were followed by Collinson, who went inside a house briefly with the two victims, although nothing “untoward” occurred inside the property.
The victims were interviewed by police following the gathering of CCTV evidence and Collinson was arrested about a month after the offences.
He was identified by both victims but remained silent in police interview.
Collinson was still on bail for the sexual offences when he sneaked inside the Grand Hotel on St Nicholas Cliff and was trying door handles at various guest rooms.
He finally found an open door to a room where a couple were sleeping.
“(The male victim) woke to find the defendant inside his room, which was in darkness,” said Mr Stephenson.
“The defendant had taken £40 from his wallet in his coat pocket. He then threw down the coat and made off.”
Police were called out to the hotel and viewed CCTV footage which showed Collinson “trying the door handles of several rooms before entering (the victims’ room) twice in quick succession”.
Officers were told there was a man who had been at the hotel who was “not a guest”.
Police found him hiding in an unoccupied room in the hotel and arrested him.
He initially told police he “couldn’t remember if he committed the offence”.
Collinson, of no fixed address, ultimately admitted three counts of sexual activity with a child, burglary and a separate offence of possessing cannabis.
He appeared for sentence on Tuesday June 7.
The court heard he had a previous conviction from 2012 for sexually assaulting a woman, which resulted in a six-week prison sentence.
He then breached his notification requirements “over the next six years”.
He had 43 previous convictions for 83 offences dating back nearly 20 years.
They included “numerous” thefts and burglaries.
His solicitor advocate David Camidge said that Collinson, a father-of-one, had drug and alcohol problems stemming from a “very difficult” upbringing.
He added that Collinson was otherwise a “hard-working man”.
Judge Sean Morris told Collinson: “I’m afraid men of your age need to understand you don’t start kissing and groping young girls.
“You were released on bail and went and burgled a hotel room where a couple were staying, and you disturbed them.
"It must have been a frightening event and you were in that hotel trying the doors, trying to steal.
"You are a prolific offender.”
Collinson was jailed for two years and made subject to a six-year sexual-harm prevention order.
He was also placed on the sex offenders’ register for 10 years.