Best E. Coast US TS for staying/trading

Hi everyone, newbie here. Doing research and changing my mind the more I learn and hear. My wife and I are traveling more, kids are out of college and we are interested in possibly buying an annual deeded week somewhere on the east coast. We were looking at somewhere in western US, as we are bigtime old west history lovers and like that area of the country. However we also are considering east coast simply because we live in PA and are thinking down the road when we don't want to necessarily fly, or cannot fly. So...that being said I need opinions on what would be the "best resort" with plenty of things to do, on and off resort, BUT would also trade well when we want to go to different locations other than our home resort. Some considerations are: we love history; looking for preferably 3 bedrooms; every year use, fixed or floating; upscale place but does not have to be luxury; reasonable maintenance fees ($800-$1000); like to horseback ride, hike. Please along with your suggestions tell me, if you know, what high or red seasons are. Anything else I should consider? Please tell me. THANKS, Jeff