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Exceptional Accommodations &
Handcrafted Bourbon

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We connect travelers with the largest selection of independently owned vacation rentals in Kentucky and Southern Indiana. In collaboration with local distilleries, cocktail bars, and restaurants, we can curate private, intimate bourbon experiences to ensure your trip to Bourbon Country is unforgettable. 

BE Our guest. Do any of these sound like you?

Bourbon Enthusiasts

Travelers who are specifically interested in visiting distilleries, tasting bourbon, and learning about the bourbon-making process. How cool would it be to bottle your own bourbon? Spoiler: very cool.



Companies planning team-building retreats, conferences, or corporate outings. Meeting spaces, high-speed internet access, and amenities for relaxation and team bonding activities.



Guests attending events in the area, such as The Kentucky Derby, music festivals, converts, bourbon tastings, sporting events, or local cultural events.

People Who

Like Money

Booking directly eliminates service fees charged by platforms like Airbnb and VRBO. So you just have to ask yourself one question, do you like money?



 Families seeking to be "present" on a unique vacation experience, exploring nearby family-friendly attractions.



 Individuals or small groups looking for a weekend getaway from nearby cities, seeking relaxation and a change of scenery.



 Those seeking a romantic escape or anniversary celebration, attracted by the cozy ambiance and intimate setting of a cozy vacation rental.



Groups of friends celebrating upcoming weddings, looking for a fun and memorable experience. Spacious accommodations, entertainment options, and proximity to nightlife for a memorable celebration.

Kentucky Derby

Talk Derby to me is THE place to book your bucket list Kentucky Derby trip.

Look no further. We roll out the red carpet for our Kentucky Derby guests. You can expect the trip of a lifetime. Derby guest perks include:


- Premium welcome package

- Anytime early check in

- Anytime late checkout

Additional services for hire:

- Custom hat making and delivery

- Private transportation

- In home chef

- Private bourbon tasting

- Private concierge

- Exclusive catering

*Limited to availability. Derby accommodations and experiences tend to sell out 6-9 months in advance.

Kentucky Derby Experiences



© 2023 Bourbon Trail Rentals, LLC d.b.a

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