Photo by Sarah Wetmore

Shepherdsville Holiday Rentals

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Holiday Rentals in Shepherdsville

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!

9.8 out of 10, Exceptional, (78)
"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 AU$689
includes taxes & fees
1 Dec - 2 Dec
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (87)
"Great location! Excellent dining options nearby!"
The price is AU$311
includes taxes & fees
14 Dec - 15 Dec
Stellar Suites

The Bellwether Hotel

2.5 star property
7.4 out of 10, Good, (8)
"Love the convenience of checking in, location, and rooms and property were gorgeous! "
The price is AU$330
includes taxes & fees
3 Dec - 4 Dec
The Bellwether Hotel

A Cozy Cottage Near the Heart of All Louisville Attractions!

10.0 out of 10, Exceptional, (337)
"This is the sweetest place! So cute and cozy. Perfect place to stay and getaway from busy life."
The price is AU$324
includes taxes & fees
2 Dec - 3 Dec
A Cozy Cottage Near the Heart of All Louisville Attractions!

Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

10.0 out of 10, Exceptional, (197)
"The cottage made for a perfect weekend getaway. It was very clean, supplied everything you could need and the owner was more than helpful to make this a special weekend for us. We plan to come back with family next time. "
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

4 rooms for rent

The price is AU$217
includes taxes & fees
25 Dec - 26 Dec
4 rooms for rent

Hancock House

3.0 star property
8.0 out of 10, Very good, (195)
"I was impressed with the room. It smelled nice, it was clean, and I really liked the design. They programmed a set of codes for me and they were easy to follow. I also felt like the parking was safe. I would definitely stay there again. "
The price is AU$241
includes taxes & fees
5 Dec - 6 Dec
Hancock House

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

9.8 out of 10, Exceptional, (59)
"Full of cobwebs and dust. Lack of pots and pans, the few there were dirty like burned food in it. Rooms nice. Yard superb Parking very nice"
The price is AU$2,058
includes taxes & fees
2 Dec - 3 Dec
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

Captain's Cabin Bed & Breakfast: Historic & Romantic

9.8 out of 10, Exceptional, (127)
"Had a great weekend at Captain's cabin. we immediately started a fire in the fireplace and enjoyed the quiet popping and warmth of the fire all weekend. Tammy's breakfasts are outstanding. Found some fun things to do in town when we finally pealed ourselves from the cabin."
The price is AU$645
includes taxes & fees
14 Dec - 15 Dec
Captain's Cabin Bed & Breakfast: Historic & Romantic

Close to Everything in Louisville!!!

9.4 out of 10, Exceptional, (28)
"Very clean and nice place close to the exposition center would stay there again."
The price is AU$370
includes taxes & fees
23 Dec - 24 Dec
Close to Everything in Louisville!!!

3 BR Downtown Sanctuary! Huge back yard

8.4 out of 10, Very good, (22)
"The property was very neat and had all the amenities it promised. The owner was great to communicate with. "
The price is AU$372
includes taxes & fees
15 Dec - 16 Dec
3 BR Downtown Sanctuary! Huge back yard

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

10.0 out of 10, Exceptional, (171)
"Excellent views of the river and downtown Louisville. We will return!!!"
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

Cabin/Vacation Home In the Woods on Private Lake Close to Louisville, Ky

10.0 out of 10, Exceptional, (162)
"Just wanted a quiet place to relax with some old friends. This fit the bill! Was taken back by the fact that we shouldn't walk in the neighborhood because we wouldn't be recognized by the association members. "
Cabin/Vacation Home In the Woods on Private Lake Close to Louisville, Ky

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

9.8 out of 10, Exceptional, (47)
"Close to the Expo for the livestock show stay. House was clean. Beds were comfortably. "
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

6BD - Riverfront Home w/ Gorgeous Views

9.2 out of 10, Wonderful, (22)
"Overall really enjoyed our stay in this home. Loved the layout! The home was well setup for our needs and Nick was fairly prompt with responses to questions. Several people from our group were talking about coming back sometime with their own families, so that says something about the enjoyment we shared here."
The price is AU$936
includes taxes & fees
2 Dec - 3 Dec
6BD - Riverfront Home w/ Gorgeous Views

Quiet and Quaint Carriage House: Sabai Sabai

9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay! The place was clean and had everything we’d need for our stay. The neighborhood was quiet yet we were still close to the action of downtown Louisville. Would definitely stay again!"
The price is AU$214
includes taxes & fees
30 Nov - 1 Dec
Quiet and Quaint Carriage House: Sabai Sabai

Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries

10.0 out of 10, Exceptional, (44)
"My wife and I stayed here over a long weekend and it was very nice! Great location, within 15 minutes of everything we wanted to do in the city. The property manager was very responsive and helpful. The room was very well kept and nicely decorated. Highly recommended "
The price is AU$226
includes taxes & fees
4 Dec - 5 Dec
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries

GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake

9.2 out of 10, Wonderful, (29)
"Property was clean, easy access. Beautiful area. We were there for the weekend of our daughters wedding in Shelbyville. "
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake

★ Victorian Louisville ★ Large 1200 sqft APT #1

9.8 out of 10, Exceptional, (136)
"We enjoyed one night at the home. Check-in was extremely easy. The home is perfect for a family of 4. Our son loved the reading nook and even slept there! We absolutely loved the VERY limited check-out process. We did not have to clean the entire home like we had to do at other VRBOs! Very easy drive to NULU. Highly recommend!"
The price is AU$298
includes taxes & fees
2 Dec - 3 Dec
★ Victorian Louisville ★ Large 1200 sqft APT #1
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 types of properties in Shepherdsville you may be interested in

22-acre Home on Bourbon Trail w/ Sunroom!

3.0 star property
22-acre Home on Bourbon Trail w/ Sunroom!

Galt House Hotel Trademark Collection by Wyndham

4.0 star property
8.8 out of 10, Excellent, (3701)
"Great hothel"
The price is AU$218
includes taxes & fees
1 Dec - 2 Dec
Galt House Hotel Trademark Collection by Wyndham

Omni Louisville Hotel

4.0 star property
9.0 out of 10, Wonderful, (1342)
"Love all the amenities and different options for food and drinks"
The price is AU$274
includes taxes & fees
30 Nov - 1 Dec
Omni Louisville Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Shepherdsville?

Yes, there are holiday rentals close to the most popular sights in Shepherdsville, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Shepherdsville. Make sure you have time to check out the riverfront and golf courses during your trip.

What are some of the best holiday rentals that Shepherdsville has to offer?

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!: This highly rated holiday home rental in Shepherdsville is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shepherdsville?

Expedia has 12 holiday rentals for your stay in Shepherdsville.

What’s there to see and do in Shepherdsville?

Bernheim Arboretum and Research Forest and Floyd's Fork are a couple of scenic spots to enjoy the outdoors, whereas Bullitt County History Museum is one of the cultural attractions. Jim Beam American Outpost and Paroquet Springs Conference Center are other places to visit while you're in town.

What are holiday rentals like in Shepherdsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shepherdsville. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip.