I always book an airbnb rather than a hotel. Stay in Georgetown or downtown Lexington and it will be the same price or less than a mid-tier hotel but more comfortable and has a kitchen. I book as soon as dates are announced - this means that I booked for this year in early May of last year.
I fly into whichever city w/in 2 hours has the best flights (combo of cost and time). This year and last year that is Cincinnati (I’m coming from Seattle). In 2015 and 2018 it was Louisville. I rent a car about 6 months out and then set an alert on Kayak and Expedia for a better deal.
We always hit the grocery / liquor store when we land and pick up breakfast, coffee, snacks, lunch fixings, and dinner for at least one night. We pack in snacks, lunch, bourbon, and water in a small backpack. This year I’m also going to toss in a good insulated mug so I’ve got ice for my water / bourbon as last year was WARM weather.
I always look for an airbnb near restaurants so if we don’t want to cook we can walk to pick up takeout or go out. At the end of the day the last thing I want to do is drive. If you do want to eat out, think about reservations ahead of time. Places are BUSY because LRK3DE usually overlaps with the last weekend of races at Keeneland.
Pack for all weather conditions - especially rain - that means it won’t rain. I specifically value having a sunhat, sunglasses, sun shirt, and sun screen. Last year my friend put a pair of flip flops in her backpack to wear in the stadium for dressage and jumping, Brilliant idea. Put a hand towel or small camping towel in your pack to dry off stadium seats if it’s raining.
I’ve never paid for parking - if you come in early enough in the morning and don’t have mobility issues the free parking is an easy enough walk in. Make sure you drop a pin in the map app on your phone. Finding the car at the end of a long day can be tough - all the fields and trees look the same.
If you can, add a few days to go bourbon tasting, catch the races at Keeneland, visit Churchill Downs, go to Daniel Boone national park, etc. It’s a beautiful part of the country and well worth being a tourist.