I have a 16ft equipment trailer. I had a F150 with trailer package and it handled the load quite well. These trailer can be purchased around $1500. Make sure that they have new trailer tires. It is not useful to have a trailer capable 7000# and the tire not load rated. Brakes!!!
If you are doing this regularly and down a tight road I guess I would recommend the same trailer with a goose neck. This arrangement can be purchased new for about double the price of the bumper pull.
Your other option is to get near the cottage, unload the tractor, drop the trailer and then move it around with the tractor.
I am thinking of selling my tractor, 955 with FEL. I could deliver with trailer for 14K.

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