Your Guide to Kentucky Derby Week—and Where to Stay

Choose from a variety of Kentucky Derby vacation rentals for the ultimate experience.

Planning a trip to the Kentucky Derby this year? We’ve got you covered!

The legendary Kentucky Derby is the culmination of the nearly two-week long Kentucky Derby Festival. Known as “The Most Exciting Two Minutes in Sports,” this much-anticipated event features far more build up than actual action, but the fun doesn’t have to end once the last horse crosses the finish line.

To experience the Kentucky Derby properly, you should plan to do far more than simply watch the race. From sipping indulgent drinks and devouring local fare to exploring the area’s arts and cultural scene, we’ve uncovered some of the must-dos in the area. Consider booking one of the many Kentucky Derby vacation rentals near Churchill Downs Racetrack for a few extra nights so you can check everything off our list and discover all that Louisville has to offer.

Where to Find Kentucky Derby Vacation Rentals

There are lots of Kentucky Derby vacation rentals to choose from on FlipKey.

Louisville is the place to be the first weekend of May each year when the Kentucky Derby rolls into town. Reserve a nearby vacation rental in advance so you can have the weekend’s festivities at your fingertips. Whether you find a place within walking distance to Churchill Downs or choose an apartment in downtown Louisville, renting a home for the event is sure to be less expensive than booking multiple (and costly!) hotel rooms for you and your group. From a cozy one bedroom rental to an historic Victorian home that sleeps 20, finding the perfect Kentucky Derby vacation rentals on FlipKey is easy.

If you’re searching for more budget-friendly options, the neighboring cities of Cincinnati and Indianapolis are also popular places to find Kentucky Derby vacation rentals. You can make it to the racetrack in under two hours from either destination and enjoy more space for less money.

Where to Eat During Kentucky Derby Week

An upscale restaurant in Louisville before patrons arrive after the Kentucky Derby.

In recent years, Louisville has emerged as a foodie city famous for its delectable cuisine. And it’s easy to see why: mouthwatering barbecue, open-faced Hot Browns, delicious Derby Pie, and sweet Bourbon Balls make the menu at many restaurants in town. From locally-owned cafes to cozy spots with warm atmospheres, here are some of FlipKey’s favorites:

Decca Restaurant | 812 East Market St., Louisville, KY 40206

Ramsi’s Cafe On the World | 1293 Bardstown Road, Louisville, KY 40204

Butchertown Grocery | 1076 E Washington St., Louisville, KY 40206

Jeff Ruby Culinary Entertainment | 325 West Main St., Louisville, KY 40202

Brasserie Provence | 150 North Hurstbourne Parkway, Louisville, KY 40222

Where to Drink During Kentucky Derby Week

An assortment of cocktails on the counter at a bar in Louisville, KY.

Whether you’re craving a craft cocktail from a trendy lounge or an iced cold beer at a funky neighborhood bar, there’s something for everyone in Louisville. With many places open as late as 2 a.m., you have the whole night to hop from place to place. Kentucky’s quintessential drinks include the famed Mint Julep (a mix of bourbon, water, crushed ice and fresh mint) and the classic Old Fashioned (muddled sugar with bitters, whiskey or brandy and a twist of citrus rind). There are plenty of options though, so head to one of these top Louisville watering holes to quench your thirst:

Garage Bar | 700 E Market St., Louisville, KY 40202

Mayan Cafe | 813 E Market St., Louisville, KY 40206

Volare Ristorante | 2300 Frankfort Ave., Louisville, KY 40206

Proof on Main | 702 West Main St., Louisville, KY 40202

RIVUE Restaurant Lounge | 140 N Fourth St., Louisville, KY 40202

What to Do During Kentucky Derby Week

Visitors tour downtown Louisville with The Thirsty Pedaler.

When you’re not recovering from race day activities in the comfort of your Kentucky Derby vacation rental, there’s lots to see and do in Louisville. Grab a seat on a pedal-propelled pubcrawler for a tour of the city or explore historic “Whiskey Row.” First time visiting Kentucky? Don’t miss the popular KentuckyShow! We recommend changing out of your festive attire, leaving the over-sized bonnet behind, and checking out the following attractions during your trip:

Speed Art Museum | 2035 South Third St., Louisville, KY 40208

Evan Williams Bourbon Experience | 528 W Main St., Louisville, KY 40202

The Thirsty Pedaler | 100 E Main St., Louisville, KY 40202

KentuckyShow! | 727 W Main St., Louisville, KY 40202

Mark Payton Glass Center | 815 W Market St., Louisville, KY 40202