Louisville, KY
The TrailHouse | 7BR Speakeasy w/Hot Tub
Step into The ALL NEW Trailhouse – Bourbon Retreat, a high-end, speakeasy-inspired Highlands estate designed for unforgettable Louisville stays. 🥃
Historic charm meets modern luxury with a sipping room, cocktail lounge kitchen, luxe bedrooms, and a private courtyard oasis with hot tub and fire pit. Perfect for Bourbon Trail adventures, Derby weekends, and elevated group getaways. With space for up to 14 guests, this home is tailor-made for gathering in style.
🛏️ ROOM FOR EVERYONE
Inside, you’ll find over 2,200 sq ft of character-filled comfort spread across three thoughtfully designed floors.
• Sleeping: Each of the 7 bedrooms is uniquely styled and furnished with a mix of queen, full, twin, and bunk beds, offering flexible sleeping arrangements for families, friend groups, or coworkers traveling together. All beds feature fresh, hotel-quality linens and cozy pillows for a restful night’s sleep.
• Bathrooms: Include tiled walk-in showers, a charming clawfoot tub, and double vanities—perfect for groups getting ready at once. 🚿
👨🍳 ENTERTAIN IN STYLE
The kitchen/lounge is a true showstopper, equipped with everything you need to cook, cater, or simply gather around the oversized island.
• Features: Stainless steel appliances, a Keurig with coffee pods and creamer, ample cookware, and plenty of dishware. It’s a central hub for the whole group. 🍳
🌿 OUTDOOR LIVING
Enjoy morning coffee on the front porch, afternoon hangs in the garden space, or unwind at night under the stars in your own slice of Highlands charm.
• Amenities: With plenty of outdoor seating, you’ll have room to spread out and soak in the experience.
📍 PRIME LOCATION
Tucked in one of Louisville’s most beloved neighborhoods, you’re truly in the middle of it all:
• 5–10 minute walk to bars, restaurants, and music venues. 🚶
• 4 minutes to KFC Yum Center and the Convention Center.
• 5 minutes to the University of Louisville.
• 9 minutes to the airport. ✈️
• Quick access to Churchill Downs, Nulu, and Downtown.
This is the perfect launchpad for exploring everything Louisville has to offer.
✨ EXCITING UPDATES
Exciting updates are on the way! A brand-new hot tub will be installed in October, and by January the home will feature a full design overhaul. The new layout will include refreshed interiors and a new bed setup with 3 king bedrooms for added comfort.
Property License: LIC-STL-25-00184
Step into The ALL NEW Trailhouse – Bourbon Retreat, a high-end, speakeasy-inspired Highlands estate designed for unforgettable Louisville stays. 🥃
Historic charm meets modern luxury with a sipping room, cocktail lounge kitchen, luxe bedrooms, and a private courtyard oasis with hot tub and fire pit. Perfect for Bourbon Trail adventures, Derby weekends, and elevated group getaways. With space for up to 14 guests, this home is tailor-made for gathering in style.
🛏️ ROOM FOR EVERYONE
Inside, you’ll find over 2,200 sq ft of character-filled comfort spread across three thoughtfully designed floors.
• Sleeping: Each of the 7 bedrooms is uniquely styled and furnished with a mix of queen, full, twin, and bunk beds, offering flexible sleeping arrangements for families, friend groups, or coworkers traveling together. All beds feature fresh, hotel-quality linens and cozy pillows for a restful night’s sleep.
• Bathrooms: Include tiled walk-in showers, a charming clawfoot tub, and double vanities—perfect for groups getting ready at once. 🚿
👨🍳 ENTERTAIN IN STYLE
The kitchen/lounge is a true showstopper, equipped with everything you need to cook, cater, or simply gather around the oversized island.
• Features: Stainless steel appliances, a Keurig with coffee pods and creamer, ample cookware, and plenty of dishware. It’s a central hub for the whole group. 🍳
🌿 OUTDOOR LIVING
Enjoy morning coffee on the front porch, afternoon hangs in the garden space, or unwind at night under the stars in your own slice of Highlands charm.
• Amenities: With plenty of outdoor seating, you’ll have room to spread out and soak in the experience.
📍 PRIME LOCATION
Tucked in one of Louisville’s most beloved neighborhoods, you’re truly in the middle of it all:
• 5–10 minute walk to bars, restaurants, and music venues. 🚶
• 4 minutes to KFC Yum Center and the Convention Center.
• 5 minutes to the University of Louisville.
• 9 minutes to the airport. ✈️
• Quick access to Churchill Downs, Nulu, and Downtown.
This is the perfect launchpad for exploring everything Louisville has to offer.
✨ EXCITING UPDATES
Exciting updates are on the way! A brand-new hot tub will be installed in October, and by January the home will feature a full design overhaul. The new layout will include refreshed interiors and a new bed setup with 3 king bedrooms for added comfort.
Property License: LIC-STL-25-00184
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Aug 8, 2026 | $1,023 | Not Available | 2 |
| Aug 9, 2026 | $509 | Not Available | 2 |
| Aug 10, 2026 | $226 | Available | 2 |
| Aug 11, 2026 | $226 | Available | 2 |
| Aug 12, 2026 | $226 | Available | 2 |
| Aug 13, 2026 | $328 | Available | 2 |
| Aug 14, 2026 | $438 | Available | 2 |
| Aug 15, 2026 | $505 | Available | 2 |
| Aug 16, 2026 | $256 | Available | 2 |
| Aug 17, 2026 | $226 | Available | 2 |
| Aug 18, 2026 | $226 | Available | 2 |
| Aug 19, 2026 | $226 | Available | 2 |
| Aug 20, 2026 | $337 | Not Available | 2 |
| Aug 21, 2026 | $470 | Not Available | 2 |
| Aug 22, 2026 | $544 | Not Available | 2 |
| Aug 23, 2026 | $319 | Available | 2 |
| Aug 24, 2026 | $254 | Available | 2 |
| Aug 25, 2026 | $226 | Available | 2 |
| Aug 26, 2026 | $263 | Available | 2 |
| Aug 27, 2026 | $568 | Not Available | 2 |
| Aug 28, 2026 | $833 | Not Available | 2 |
| Aug 29, 2026 | $1,018 | Not Available | 2 |
| Aug 30, 2026 | $421 | Available | 2 |
| Aug 31, 2026 | $226 | Available | 2 |
| Sep 1, 2026 | $226 | Available | 2 |
| Sep 2, 2026 | $294 | Available | 2 |
| Sep 3, 2026 | $486 | Available | 2 |
| Sep 4, 2026 | $1,009 | Available | 3 |
| Sep 5, 2026 | $1,297 | Available | 3 |
| Sep 6, 2026 | $776 | Available | 2 |
| Sep 7, 2026 | $312 | Available | 2 |
| Sep 8, 2026 | $226 | Available | 2 |
| Sep 9, 2026 | $229 | Available | 2 |
| Sep 10, 2026 | $698 | Not Available | 2 |
| Sep 11, 2026 | $1,234 | Not Available | 2 |
| Sep 12, 2026 | $1,338 | Not Available | 2 |
| Sep 13, 2026 | $506 | Available | 2 |
| Sep 14, 2026 | $226 | Available | 2 |
| Sep 15, 2026 | $242 | Available | 2 |
| Sep 16, 2026 | $948 | Available | 4 |
| Sep 17, 2026 | $1,188 | Available | 3 |
| Sep 18, 2026 | $1,632 | Available | 3 |
| Sep 19, 2026 | $1,951 | Available | 3 |
| Sep 20, 2026 | $1,246 | Available | 2 |
| Sep 21, 2026 | $465 | Available | 2 |
| Sep 22, 2026 | $277 | Available | 2 |
| Sep 23, 2026 | $583 | Available | 4 |
| Sep 24, 2026 | $2,520 | Not Available | 3 |
| Sep 25, 2026 | $3,172 | Not Available | 3 |
| Sep 26, 2026 | $3,288 | Not Available | 3 |
| Sep 27, 2026 | $2,113 | Not Available | 2 |
| Sep 28, 2026 | $354 | Available | 2 |
| Sep 29, 2026 | $259 | Available | 2 |
| Sep 30, 2026 | $334 | Available | 2 |
| Oct 1, 2026 | $1,461 | Not Available | 2 |
| Oct 2, 2026 | $1,463 | Not Available | 2 |
| Oct 3, 2026 | $1,463 | Not Available | 2 |
| Oct 4, 2026 | $539 | Available | 2 |
| Oct 5, 2026 | $294 | Available | 2 |
| Oct 6, 2026 | $229 | Available | 2 |
| Oct 7, 2026 | $294 | Available | 2 |
| Oct 8, 2026 | $1,156 | Not Available | 2 |
| Oct 9, 2026 | $1,158 | Not Available | 2 |
| Oct 10, 2026 | $1,206 | Not Available | 2 |
| Oct 11, 2026 | $680 | Not Available | 2 |
| Oct 12, 2026 | $680 | Not Available | 2 |
| Oct 13, 2026 | $680 | Not Available | 2 |
| Oct 14, 2026 | $680 | Not Available | 2 |
| Oct 15, 2026 | $807 | Not Available | 2 |
| Oct 16, 2026 | $1,200 | Available | 2 |
| Oct 17, 2026 | $1,155 | Available | 2 |
| Oct 18, 2026 | $601 | Available | 2 |
| Oct 19, 2026 | $431 | Available | 2 |
| Oct 20, 2026 | $700 | Not Available | 2 |
| Oct 21, 2026 | $728 | Not Available | 2 |
| Oct 22, 2026 | $1,091 | Not Available | 2 |
| Oct 23, 2026 | $1,046 | Available | 2 |
| Oct 24, 2026 | $1,114 | Available | 2 |
| Oct 25, 2026 | $716 | Available | 2 |
| Oct 26, 2026 | $352 | Available | 2 |
| Oct 27, 2026 | $313 | Available | 2 |
| Oct 28, 2026 | $381 | Available | 2 |
| Oct 29, 2026 | $776 | Available | 2 |
| Oct 30, 2026 | $973 | Available | 2 |
| Oct 31, 2026 | $1,016 | Available | 2 |
| Nov 1, 2026 | $596 | Available | 2 |
| Nov 2, 2026 | $321 | Available | 2 |
| Nov 3, 2026 | $272 | Available | 2 |
| Nov 4, 2026 | $350 | Available | 2 |
| Nov 5, 2026 | $1,189 | Not Available | 2 |
| Nov 6, 2026 | $1,190 | Not Available | 2 |
What this home offers
Where you’ll be
Louisville, KY, 40204, US
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You’ll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We’re building a relationship, not closing a booking.
Things to know
Check-in & check-out
Check-in after 4:00 PM.
Check-out before 10:00 AM.
Property rules
Children welcome (2–12 years).
Infants welcome (under 2).
Maximum 14 guests.
No pets allowed.
No parties or events.
Number and age of guests
Pets
Events
Smoking
Check-in & check-out
Cancellation policy
Contact us for cancellation policy details prior to booking.









