Four Borders businesses and another nearby were targeted by raiders in the space of a few hours on Sunday morning.
The Glentress Hotel near Peebles and a hair salon in Eyemouth were burgled, Coldingham Post Office was broken into but nothing was stolen and a failed attempt was made to raid Tweed Road Stores in Galashiels.
Police are appealing for any witnesses to the raids and attempted break-ins to call them on 101 or Crimestoppers on 0800 555111.
The apparent crime spree might have started in West Linton at around 11.30pm on Saturday when the door of a house was damaged, but no entry was gained.
A café nearby in Leadburn, Midlothian, was then raided at around 1.30am on Sunday and the Glentress Hotel was burgled at around 2.15am, four-figure sums of cash being stolen in both cases.
The abortive raid on Tweed Road Stores followed at around 2.30am.
The would-be raiders used a chisel in a bid to smash the reinforced glass door of the Adam Purves-owned premises but failed to get in.
Richard Garrie, regional manager for the Borders retail, garage and property chain, was enjoying a weekend break in Blackpool in Lancashire when he received a call from his son Ryan after he opened the shop at 6.30am.
“Ryan told me the glass on the front door was badly cracked and assumed it had been vandalised, but when I returned to Galashiels at about 1pm and viewed the footage from the eight security cameras inside the shop, the reality of what had happened became evident,” said Mr Garrie.
“Two men, wearing balaclavas with slits for their eyes, pulled up in a Peugeot 106 car on the pavement outside the shop, got out and started trying to smash our front door with a chisel. It was chilling viewing.
“They appeared to be disturbed by a passing motorist, but instead of driving off, they hid in their car and then returned eight minutes later to have another go.
“They must have known that if they had entered the shop the alarm linked would have gone off, but they seemed unconcerned and oblivious to the fact there were lots of houses around.
“Fortunately, the reinforced glass did its job, and they eventually gave up and sped off.”
Mr Garrie said the raid had left his staff feeling “naturally a bit shaken and vulnerable”.
“Up to now, a single shop assistant has been on duty in the early mornings and in the evening, so, for the time being, I’m making sure there are always at least two staff there at these times,” he added.
Following the abortive raid on the Galashiels convenience store, a hairdresser’s in Eyemouth in Berwickshire was broken into at 3.30am and goods and a three-figure sum of cash were taken.
Finally, the post office in Coldingham was broken into at 3.40am but nothing was taken.
Police are uncertain whether the raids and attempted break-ins are linked, despite some being many miles apart, but are not ruling out the same culprits being responsible.
Detective constable Callum Peoples, of Galashiels CID, said: “We are keen to hear from anyone who saw anything suspicious in these areas on Saturday night or early Sunday morning.
“We are following all lines of inquiry and keeping an open mind as to whether these incidents are linked.”