Photo by Sarah Wetmore

Shepherdsville Vacation Rentals

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Browse Select Shepherdsville Vacation Homes

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Fridge, coffee/tea maker, cookware/dishes/utensils

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (20)
"Wonderful set up for our ladies weekend. Tyler was easy to work with and very responsive. Jeffersonville is a hidden gem!"
The price is CA $145
CA $510 total
includes taxes & fees
Dec 26 - Dec 27
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Historic District Townhouse in City's BEST Location
Fridge, microwave, oven, stovetop

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (183)
"This was a great stay and the property was so well-managed! Super easy to check in, everything was in great condition. Comfortable beds, and pretty much anything you need in the kitchen. The property was spotless. They provide white noise machines to mask outdoor noises, since it's on a commercial strip, but we didn't need them. Just note that you do need to climb stairs to get to the bedrooms. Deirdre was super-responsive to questions. Highly recommend."
Historic District Townhouse in City's BEST Location
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
Fridge, microwave, oven, stovetop

River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

9.8 out of 10, Exceptional, (50)
"Close to the Expo for the livestock show stay. House was clean. Beds were comfortably. "
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Exterior

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (137)
"Stayed for a few nights with family over Thanksgiving. Communication with James was outstanding. The house is exactly as pictured, which means it is interesting and beautiful, combining modern comforts with original beauty. Neighborhood could not have been better - quiet but with extremely easy walking access to a ton of stuff. Highly recommend!"
The price is CA $268
CA $563 total
includes taxes & fees
Dec 30 - Dec 31
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Exterior

Near Highways and a 20 Min Drive to Louisville's Main Attractions

10.0 out of 10, Exceptional, (33)
"The house was a great location for doing a lot of the distilleries. With my big group we had no problems with places to sleep and hang out. A+++"
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Fridge, microwave, oven, stovetop

Newly Renovated Studio! Ideal location for walking to restaurants & shops

9.8 out of 10, Exceptional, (23)
"Place was very clean and cozy. Easy to get in and out and owner was very responsive. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail

9.8 out of 10, Exceptional, (26)
"Property was clean and had amenities we needed. Great place to stay as a starting point to other points of interest. Needed to be careful where you went in some surrounding neighborhoods."
The price is CA $109
CA $391 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown
Fridge, microwave, oven, stovetop

Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown

The price is CA $151
CA $269 total
includes taxes & fees
Dec 29 - Dec 30
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
Interior

Derby Cigar & Bourbon Lounge Group Stays in charming Louisville

The price is CA $271
CA $783 total
includes taxes & fees
Dec 26 - Dec 27
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
Terrace/patio

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10.0 out of 10, Exceptional, (25)
"Quality family time. Spacious space. inviting "
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
The Trifecta in Old Louisville
5 bedrooms, iron/ironing board, travel crib, free WiFi

The Trifecta in Old Louisville

10.0 out of 10, Exceptional, (109)
"House is exactly as advertised. Host very responsive and accommodating. Nice location. We had a great stay, thank you!"
The Trifecta in Old Louisville
Cozy Louisville Home w/ Spacious Yard & Parking
Exterior

Cozy Louisville Home w/ Spacious Yard & Parking

10.0 out of 10, Exceptional, (8)
"This little house is a hidden gem! I booked it as it was close to the U of L hospital where my husband was to have major surgery. It was absolutely perfect for my needs. I didn’t get to enjoy it much as I was mainly just there to shower and catch a little sleep. The houses along this street are cute and well maintained. I felt safe there even tho I was alone. There are some homes a few blocks away that are a little questionable, but the homes near here are adorable. I would definitely stay...
Cozy Louisville Home w/ Spacious Yard & Parking
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home
Fridge, microwave, oven, cookware/dishes/utensils

7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

10.0 out of 10, Exceptional, (15)
"Was in Louisville for a bachelor party (20 of us). The house was amazing! Plenty of space, very clean, great location. Would definitely recommend for larger groups."
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
Fridge, microwave, oven, stovetop

Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi

10.0 out of 10, Exceptional, (59)
"Very nice. Beautifully decorated "
The price is CA $109
CA $292 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
5BR Very Spacious Home! Perfect for Family!
Fridge, microwave, oven, stovetop

5BR Very Spacious Home! Perfect for Family!

8.8 out of 10, Excellent, (9)
"We had a great stay! Beautiful home in a safe and quiet neighborhood. Great communication with host. Comfortable accommodations for 10 adults. Easy access to Freedom Hall where our event was hosted."
The price is CA $142
CA $564 total
includes taxes & fees
Dec 30 - Dec 31
5BR Very Spacious Home! Perfect for Family!
Cozy, historic, pet-friendly home!
Private kitchen

Cozy, historic, pet-friendly home!

9.8 out of 10, Exceptional, (14)
"The home is just as it appears in the photos....very charming and entertaining with seasonal decorations. The home was clean and comfortable. We enjoyed the gas firepit outside after touring the town. We will return during this season as the decorations for walking tours and historical site visits were amazing. Great location."
The price is CA $352
CA $560 total
includes taxes & fees
Dec 30 - Dec 31
Cozy, historic, pet-friendly home!
16 Mi to Louisville: Pet-Friendly Getaway!
TV

16 Mi to Louisville: Pet-Friendly Getaway!

10.0 out of 10, Exceptional, (2)
"Clean, up to date, well stocked with the basics. Enough seating to allow a small group to comfortably interact, decent kitchen able to cook almost anything. All appliances in great working order. We arrived, had dinner, then went to bed. The next day we visited a local distillery and enjoyed a meal in Louisville. Went back to the Vrbo and watched some TV and left the next day."
16 Mi to Louisville: Pet-Friendly Getaway!
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Interior

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (61)
"Really enjoyed the house, very spacious. Great host as well, would recommend staying here!"
The price is CA $932
CA $1,805 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Fridge, microwave, oven, stovetop

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

9.8 out of 10, Exceptional, (80)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is CA $215
CA $636 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
Fridge, microwave, oven, stovetop

The Orange Door ~ Prime Germantown 4BR/2BA Luxury

10.0 out of 10, Exceptional, (19)
"It was pretty solid no real complaints."
The price is CA $228
CA $569 total
includes taxes & fees
Jan 5 - Jan 6, 2025
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
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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Other property types in Shepherdsville

22-acre Home on Bourbon Trail w/ Sunroom!
Interior

22-acre Home on Bourbon Trail w/ Sunroom!

3.0 star property
22-acre Home on Bourbon Trail w/ Sunroom!
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Fridge, microwave, oven, stovetop

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

9.8 out of 10, Exceptional, (80)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is CA $215
CA $636 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (89)
"Outstanding!"
The price is CA $191
CA $297 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Stellar Suites
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.