The couple's solicitor had tried to argue moving them from the land, in an area of outstanding natural beauty, breached their human rights.
Mrs Pryke's family has lived in the popular commuting village since the 1600s and the couple were married at the local church.
The 48-year-old mother-of-three, fought back tears after hearing her husband would be starting his jail sentence.
She said: "The judge told me I have got to reflect whilst Asa is in prison because when he is out, they could apply for a warrant and I could be jailed.
"It was so upsetting - we tried to say 'how can you do such a thing and why do you think it is right?' The judge just told us he was upholding the law."
Some residents living in the village have welcomed the ruling.
One, who asked not to be named, said: "This is a lovely area to live and people have been upset by the sight of the caravans and tents. The law is the law and although it may seem extreme for this gentleman to be jailed, it certainly could have been avoided.
"It's sad to see what has happened to the family but really, one can only have so much sympathy because they were given a lot of warning of what was going to happen."
Speaking before the ruling Mr Pryke, who is now working as a specialist insurance broker, said: "We are fighting to stay on our land and fighting for what we believe in.
"This country needs 'doers' to get out of the mess it is in, not just people who are happy just to take handouts.
"We would rather stand on our own feet and live on our land than take taxpayers' money for housing support. How can making us homeless make any sense when we will be forced to live off state handouts?"
The couple were hoping to get planning permission from Colchester Borough Council for their eco-friendly home.
Mr Pryke added: "We would even be prepared to build one home and then give land away for another for social housing. That is how committed we are to this project.
"We moved onto here to live in tents because we were desperate and did not want to be holed up in a council flat.
"Of course the laws mean we are forbidden from developing the land without planning permission but when the weather turned on us last winter and we were offered the loan of caravans, then we jumped at the chance because we did not want to freeze to death in the cold."
The couple said they were only offered "unsuitable" accommodation from the local council in flats and homes which are too small and they don't want to be at the mercy of unscrupulous landlords.
Earlier this year, the couple were given four-month suspended prison sentences, for failing to comply with an earlier order to leave. It is that sentence against Mr Pryke which has now been activated.
Tim Young, Colchester borough councillor in charge of planning, said: "The council has gone through every route possible to assist and advise the family but it has gone to court.
"The judge has come up with a sensible judgement because the children are important in all this."
