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Fall 2016 England andScotland

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This will be our first trip to the UK and would love some help planning.
A few questions here:
#1 We plan to spend about 14 days in the UK (flying from the USA) after the tourist season is over in 2016 (Possibly September) Is the timing good regarding weather, crowds, and tickets?
#2 We have friends in London and family in Cheltenham. 4 of the days will be spent with them doing touristy stuff in their areas. Should we reserve hotels ahead of time in our other destinations?
#3 We would like to visit Oxford, Althorp estate, my husband's ancestral home in Ashbourne, Durham, Edinburgh, Liverpool and Caernarfon Castle in Wales, Minton in Shropshire (this could be scrapped), Cheltenham - 2 days to visit with family, Iron Acton (my ancestral town), Stonehenge and then about 3 days in London. Is this too much to pack into 14 days?
#4 Transportation .... I know we can do bus tours whilst in London and in Edinburgh, but what is the best mode of transportation for the countryside? If we do ride the train through the countryside, are there taxis in each town that can get you from the station to your tourist site? Would renting a car be better for us, since we want to stop in non-touristy random places?
#5 Would a day trip to Paris from London be out of the question, as far as time?
Thanks in advance for all your help!!

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