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! 🥃🏇🏻🍗

28 properties  

$552-8,999/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!

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$649-6,999/night

The Oak Barrel Lodge

6 Bedrooms • 6 Baths (4 full, 2 half) • Sleeps 2-18
Internet Downtown
Space, space, and more space! Located only 5 minutes from Downtown Louisville and Distilleries! Sleeps 18 people on 9 queen beds, 4 full bathrooms and 2 additional 1/2 bathrooms. Great for groups and wedding parties! Private parking lot with 10 spaces, trailers and RVs welcome!

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$306-5,499/night

The Norton Commons Luxe

5 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 1-12
Internet Hot Tub

Experince a luxury accommodation within Louisville's most prestigious neighborhood at The Norton Commons Luxe.

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$177-4,149/night

Bourbon House 1 | Expo Center - Private Backyard

5 Bedrooms • 2 Baths • Sleeps 4-12
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!!

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$209-5,020/night

Bourbon House 2 - 4BR/2.5BA Sleeps 12!

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 1 and Bourbon House 3 as well!)

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$329-6,681/night

Bourbon House 3 - Luxurious Group Accommodation

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

Brand new construction in the heart of historic Germantown!

Now leasing to large groups. Book today!

 

Bourbon House 3, is located in the very walk-able Germantown Neighborhood that’s buzzing with nightlife, restaurants, coffee shops and pubs, this HUGE (5-bedroom), (3,5 bath) stunner is perfect for groups of up to 20 people! Sleep in comfort on the New Sealy Posturepedic Hybrid mattresses and enjoy the private dressing areas for each bed!

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$99-3,499/night

Bourbon House 4 - The Wellingmoor

3 Bedrooms • 2 Baths • Sleeps 1-8
Internet Hot Tub
Welcome to The Wellingmoor, the 4th and newest addition to the Louisville Bourbon House collection of properties. Southern Charm meets Modern Convenience at this fully remodeled brick ranch. Perfect for groups of up to 8, you'll be right in the middle of Bourbon Country. Just a few blocks from the famous Bardstown Road Highlands, you can shop, sip, eat, and explore....oh and did we mention you can come back home to a hot, relaxing, bubbly hot tub!

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$142-1,618/night

Excellent 3BR/2BA PRIME Location!

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.

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$122-1,325/night

Lovely 3BR/1BA PRIME Location!

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.

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$306-4,149/night

6BR/3BA PRIME Location - Entire Home (Both Units)

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.

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$177-4,149/night

Luxurious Corporate/Derby Rental

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.

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$410-5,499/night

The Bluegrass Ranch - Secluded Luxury Cabin

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.

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