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Shepherdsville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Shepherdsville vacation homes

A spacious living room with two leather sofas, a coffee table, and a ceiling fan.

1. Modern Comfort •Bourbon Trail & Derby•Fenced yard•full kitchen•parking

Modern Comfort •Bourbon Trail & Derby•Fenced yard•full kitchen•parking
Shepherdsville
10.0 out of 10, Exceptional, (6 reviews)
"Very welcoming of pets, and the host was very accommodating for our stay. Would stay here again for sure!"
United States
Jeffrey F.
The price is CA $217
CA $509 total
includes taxes & fees
Oct 28 - Oct 29
Modern Comfort •Bourbon Trail & Derby•Fenced yard•full kitchen•parking
A kitchen with a granite countertop, stainless steel sink, wooden cabinets, a decorative soap dispenser, and a television mounted on the wall.

2. The Derby House - Relaxing retreat before and after the excitement of the Derby!

The Derby House - Relaxing retreat before and after the excitement of the Derby!
Louisville
9.4 out of 10, Exceptional, (22 reviews)
"She was absolutely wonderful!! Our family had a wonderful time!!"
United States
ashley C.
The Derby House - Relaxing retreat before and after the excitement of the Derby!
A hot tub on a wooden deck with a house in the background.

3. Hot Tub- Sleeps 10- Bourbon Trail- Historic Home

Hot Tub- Sleeps 10- Bourbon Trail- Historic Home
Coxs Creek
10.0 out of 10, Exceptional, (27 reviews)
"We stayed here on a girl’s getaway and were very pleased with the accommodations!"
United States
Cathy A.
The price is CA $285
CA $447 total
includes taxes & fees
Oct 25 - Oct 26
Hot Tub- Sleeps 10- Bourbon Trail- Historic Home
A modern kitchen with white cabinets, a black countertop, and a stainless steel refrigerator.

4. Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
Radcliff
9.8 out of 10, Exceptional, (26 reviews)
"Very clean, enjoyed our stay. location was close to town."
United States
william w.
The price is CA $101
CA $260 total
includes taxes & fees
Oct 25 - Oct 26
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
A living room with a fireplace, leather armchairs, a coffee table, and a painting on the wall.

5. New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
South Louisville
9.8 out of 10, Exceptional, (49 reviews)
"Great stay and great host"
United States
Chayil B.
The price is CA $125
CA $331 total
includes taxes & fees
Nov 9 - Nov 10
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
A backyard with a fire pit, outdoor seating, and a covered patio area.

6. Bourbon Trailhead Bardstown

Bourbon Trailhead Bardstown
Bardstown
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful property, we’ll be back! Great location close to town but quiet and peaceful in the evenings. House was very clean, hot tub was perfect for stargazing, covered back patio was ideal for grilling."
United States
Michelle O.
The price is CA $457
CA $973 total
includes taxes & fees
Nov 1 - Nov 2
Bourbon Trailhead Bardstown
A wooden deck with a table set for dining, overlooking a grassy area and a building in the distance.

7. Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square

Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
Coxs Creek
10.0 out of 10, Exceptional, (23 reviews)
"The house was beautiful and clean and we had a great time on our trip. Would stay again"
United States
Nick F.
The price is CA $489
CA $1,139 total
includes taxes & fees
Oct 26 - Oct 27
Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
A bedroom with a bed, nightstands, a ceiling fan, and a window with shutters.

8. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is CA $178
CA $383 total
includes taxes & fees
Nov 9 - Nov 10
Convenient & Cozy! Close to everything Louisville!
A multi-level home interior with a wooden staircase, a loft bedroom, and decorative wall plates.

9. Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!

Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!
Bardstown
10.0 out of 10, Exceptional, (36 reviews)
"We had an amazing time and the house was perfect! We would definitely stay again. "
United States
Laura D.
The price is CA $350
CA $857 total
includes taxes & fees
Nov 3 - Nov 4
Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!
A living room with a sofa, armchair, coffee table, and a dining area with a table and chairs.

10. The Whiskey Stop! A Spacious Highlands Retreat

The Whiskey Stop! A Spacious Highlands Retreat
Germantown
10.0 out of 10, Exceptional, (79 reviews)
"It was perfect for our stay very comfortable and we enjoyed it very much"
United States
Lester W.
The price is CA $96
CA $267 total
includes taxes & fees
Nov 9 - Nov 10
The Whiskey Stop! A Spacious Highlands Retreat
A two-story brick house with a front entrance, a small front yard with plants, and a clear blue sky.

11. Stay in a historic Early 1800s Guest House!

Stay in a historic Early 1800s Guest House!
Bardstown
9.8 out of 10, Exceptional, (140 reviews)
"We loved our time at this property! Great location and beautiful neighborhood. Easy walk to nearby shops and restaurants. Would stay here again."
United States
Debbie B.
The price is CA $146
CA $266 total
includes taxes & fees
Oct 25 - Oct 26
Stay in a historic Early 1800s Guest House!
A covered porch with a brick wall, a chair, and a view of a residential area.

12. Renovated Radcliff KY Townhome near Fort Knox & Elizabethtown + EV Charger

Renovated Radcliff KY Townhome near Fort Knox & Elizabethtown + EV Charger
Radcliff
8.8 out of 10, Excellent, (12 reviews)
"Some small maintenance issues, but was perfect for our needs. The four recliners(!) were a big plus."
United States
Elden T.
The price is CA $118
CA $320 total
includes taxes & fees
Oct 25 - Oct 26
Renovated Radcliff KY Townhome near Fort Knox & Elizabethtown + EV Charger
A modern kitchen with a central island, white cabinetry, and a variety of decorative items on the walls.

13. Large Louisville Home Near Expo, Airport & UofL

Large Louisville Home Near Expo, Airport & UofL
3.0 star property
Louisville
10.0 out of 10, Exceptional, (1 review)
"⭐⭐⭐⭐⭐ We had a great stay! The host’s communication was excellent from start to finish and made everything very easy. The location was perfect—very convenient to the Expo Center, where our event was located - and the house was spacious with plenty of room for everyone. We did run into one minor issue during our stay, but the host responded immediately and resolved it right away. That level of responsiveness was greatly appreciated. Overall, we had a wonderful experience and would definitely...
United States
Cashundrea
The price is CA $374
CA $759 total
includes taxes & fees
Oct 25 - Oct 26
Large Louisville Home Near Expo, Airport & UofL
A patio with Adirondack chairs, a fire pit, and a small shed in a garden setting.

14. Spacious Highlands gem near Bellarmine & Bardstown

Spacious Highlands gem near Bellarmine & Bardstown
Belknap
10.0 out of 10, Exceptional, (4 reviews)
"The property was perfect for quick family gathering. John was a great host. He was super responsive and I would glad rent from him again."
United States
Laura C.
The price is CA $166
CA $526 total
includes taxes & fees
Oct 25 - Oct 26
Spacious Highlands gem near Bellarmine & Bardstown
A living room with a sectional sofa, a fireplace, a flat-screen TV, and a zebra-patterned chair.

15. Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row

Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
Clarksville
9.0 out of 10, Wonderful, (13 reviews)
"Was a great time and very clean "
United States
Jeff B.
The price is CA $79
CA $265 total
includes taxes & fees
Oct 28 - Oct 29
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
A modern living room with a sofa, a glass coffee table, and a TV mounted on the wall.

16. Spacious 3BD Luxury Stay

Spacious 3BD Luxury Stay
Louisville
9.0 out of 10, Wonderful, (26 reviews)
"Very clean, had everything we needed for a weekend stay. Would stay here again if ever back in the area"
United States
Courtney H.
The price is CA $234
CA $477 total
includes taxes & fees
Oct 26 - Oct 27
Spacious 3BD Luxury Stay
A dining area with a black table and chairs, a vase with dried plants, and wall-mounted wooden coasters with text.

17. Spacious family-friendly stay with arcade fun!

Spacious family-friendly stay with arcade fun!
Wilder Park
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic location, with Churchill Downs a short distance away, and a Kroger in walking distance. Off street parking is always a plus, and the host is responsive. The place is beautiful and clean."
United States
Leah L.
The price is CA $105
CA $334 total
includes taxes & fees
Oct 25 - Oct 26
Spacious family-friendly stay with arcade fun!
A kitchen with white cabinets, a black refrigerator, a stove, and a dishwasher.

18. The E-Town Retreat 2BR townhouse close to Downtown

The E-Town Retreat 2BR townhouse close to Downtown
Elizabethtown
9.4 out of 10, Exceptional, (14 reviews)
"Nice place"
United States
Natalie G.
The price is CA $124
CA $253 total
includes taxes & fees
Oct 25 - Oct 26
The E-Town Retreat 2BR townhouse close to Downtown
A patio with a table and chairs, surrounded by a wooden fence and tall, conical trees.

19. Bourbon Belle- Cozy Germantown home with parking!

Bourbon Belle- Cozy Germantown home with parking!
Germantown
10.0 out of 10, Exceptional, (79 reviews)
"We've stayed here a few times in the past and it's always been a great experience!"
United States
Paul H.
The price is CA $76
CA $242 total
includes taxes & fees
Nov 1 - Nov 2
Bourbon Belle- Cozy Germantown home with parking!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

20. The Maple Den

The Maple Den
Elizabethtown
9.8 out of 10, Exceptional, (26 reviews)
"Wonderful hosts and beautiful clean home!Perfect location!"
United States
Lisa H.
The price is CA $165
CA $418 total
includes taxes & fees
Oct 26 - Oct 27
The Maple Den
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shepherdsville Hotel Reviews

Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

10/10 Excellent
"enjoyed our one night stay at this hotel. front desk friendly, room clean and breakfast fine."
Jeffery L 1-night trip
Posted 4 hours ago
Wingate by Wyndham Louisville Fair and Expo

Find out more about Shepherdsville

Shepherdsville Vacation Homes information

Number of reviews
564
Accommodation
933 Vacation Homes
Lowest Price
CA $242
Highest Price
CA $1,313

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