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Renting a House boat in August at Dale Hollow. Where is the best place to party at? We are renting out of Holly Creek.

No real big party coves there. Every place is a party. Holly Creek is pretty good. I've gone there the last two years. For your trip, Sulphur Creek is about 45 minutes closer and the ramp is not anywhere near as winding and hard to get to. I am from Terre Haute and drag a 46' Cig down there. Very hard to get down to the lake at Holly Creek. For a good party area, try the cliffs at Wolf Creek. There are always a lot of boats that tie up there, party down, and jump off the cliffs. PM me for more info. Great houseboat lake. I will be there in June and July this year.
Ron

I will be pulling a 23' Bayliner with a 2500 Crew cab 6ft bed. Will there be any problems?

No you shouldn't have problems with that. There are a couple of 90 degree turns going down to the lake that make a 46' boat almost impossible. I had to have another vehicle drive in front of me to wave off traffic. We also pulled my 23 Rinker and had absolutely no problems with it at all.