We connect travelers with the largest selection of independently operated vacation rental homes available for the Kentucky Bourbon Trail, Kentucky Derby, and all things Kentucky has to offer! 🥃🏇🏻🍗

25 properties  

$599-2,199/night

Persimmon Ridge Lodge

7 Bedrooms • 6 Baths (4 full, 2 half) • Sleeps 9-18
Internet
You will be telling everyone you know about your stay! 8,000 sq. ft. golfer's paradise features indoor putting green and practice cage. 7 king beds, 2 queen beds, 4 full bathrooms, 2 half bathrooms. Great for wedding parties! Ask about the available golf courses when you stay with us!

Photos Details Inquire


5 Bedrooms • 2 Baths • Sleeps 8-12
Internet

Welcome to Louisville, Kentucky! Home of Bourbon Trail Adventures, and the Kentucky Derby!

Exclusively offered by the Bourbon Trail Rentals family of properties! Welcome to the Louisville Bourbon House, where your comfort and relaxation is our top priority! Located about 1⁄2 mile from the Kentucky Fair and Exposition Center, the Bourbon House is as close as you can get to all of the festivals, concerts, sports tournaments, and Kentucky State Fair!!

Photos Details Inquire


4 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 5-10
Internet

The Newest Addition to the Louisville Bourbon House Collection, Bourbon House 2 will not disappoint! From the Gourmet Kitchen to the Spacious Bedrooms with Sealy Hybrid mattresses, this Charming 1920’s era Bungalow has been “opened up” to create group space and yet still has many separate sitting areas!

With Professional Management and Professional Ownership, this place shines brightly! Book Today!

(Check reviews for the Bourbon House also)

Photos Details Inquire


5 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 10-20
Internet

The wait is over!

Bourbon House 3 is the newest (and biggest!) luxury accommodation in the Louisville Bourbon House collection.

Located in the heart of Historic Germantown, this HUGE 5 bedroom, 3.5 bath stunner is perfect for groups of up to 20 people! Germantown is a walkable neighborhood buzzing with night life, restaurants, coffee shops, and pubs. Private off-street parking for up to 4 vehicles is available and extremely rare for this neighborhood.

Built new in 2022, BH3 has all of the modern amenities and touches that you would expect from a 21st century new construction.

Photos Details Inquire


3 Bedrooms • 2 Baths • Sleeps 3-6
Internet Fireplace
NEWLY RENOVATED 3 Bed 2 Bath lower level of duplex is perfect for small groups, couples, or business travelers. Upon arrival you'll be greeted by the brand new remodeled kitchen and open concept living space. The quaint sitting area is perfect for taking a break from the day's activities.

Photos Details Inquire


3 Bedrooms • 1 Bath • Sleeps 3-6
Internet
NEWLY RENOVATED 3 Bed 1 Bath upper level of duplex is perfect for small groups, couples, or business travelers. Upon arrival you'll be greeted by the brand new remodeled kitchen and open concept living space. The quaint sitting area is perfect for taking a break from the day's activities.

Photos Details Inquire


6 Bedrooms • 3 Baths • Sleeps 6-12
Internet Fireplace
NEWLY RENOVATED duplex is perfect for groups! Upstairs unit is 3BR/1BA and the first floor unit is 3BR/2BA. Your group will have access to the entire home (both units) during your stay.

Photos Details Inquire


$189-419/night

11004 Booker Rd

3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 4-8
Internet Fireplace

Perfect accommodations for a Corporate Stay, Bourbon Trail Adventures, and The Kentucky Derby!

The house is extremely private, yet offers all the conveniences of the city in one of Louisville’s high end neighborhoods.

Photos Details Inquire


5 Bedrooms • 3 Baths • Sleeps 9-10
Internet Wood Stove Hot Tub

From the moment you turn into our driveway, you''' know that you've come to a special place. The ranch post arch welcomes you to The Bluegrass Ranch!

This amazing property is nestled on 22 secluded acres. The log cabin style home gives all the feels of a mountain style escape, combining all of the comforts of modern amenities. The first thing you'll notice is the wrap around porch with numerous outdoor seating areas to relax and enjoy the beautiful, un-evaded views of the sunset.

Photos Details Inquire


3 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 3-6
Internet Fireplace River
You will be telling everyone you know about your stay! Give yourself a special treat! Tranquil and beautiful describes this home with breathtaking views from every window. Boat ramp down the street. Conveniently located just across the bridge from Louisville’s most prestigious neighborhood. You’ll love all the privacy, but will only be 15-20 drive to all Louisville and Southern Indiana restaurants and shopping!

Photos Details Inquire


$189-399/night

2703 Summerfield Dr

3 Bedrooms • 3 Baths • Sleeps 5-8
Internet
NEWLY RENOVATED 3 bedrooms (4 beds) with a bonus sleeping area in the basement, 3 full bathrooms. This entire home is perfect for professionals traveling to Louisville. Upon arrival you'll be greeted by the fresh, open concept living space. Sleeps 8 in beds.

Photos Details Inquire


$149-299/night

The Chuckwick House

4 Bedrooms • 3 Baths • Sleeps 6-10
Internet

Perfect accommodations for foodies, soccer fans, Bourbon Trail adventures, and The Kentucky Derby!

Perfect location near, downtown, Paristown Point, Churchill Downs, football/baseball/soccer stadiums, and convention center.

Photos Details Inquire

1 – 12 of 25 places to stay