Photo by Sarah Wetmore

Holiday Homes in Shepherdsville

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Featured Holiday Homes in Shepherdsville

Stay in a historic Early 1800s Guest House!

10.0 out of 10, Exceptional, (88)
"Very cute Guest House. 1 block from Main St. close to restaurants and bars. Clean, great wifi, tv and comfi bed. Owners are responsive and there if you need them. Price was great. Would rent again."
The price is AU$297
includes taxes & fees
2 Dec - 3 Dec
Stay in a historic Early 1800s Guest House!

RIVERFRONT - Boat Slips - 10 Min to Dtown Lville

10.0 out of 10, Exceptional, (121)
"We (myself and my 12, 15, and 17 year old children) took a last minute fall break trip down south and chose this amazing home to stay in for a couple nights. WOW, did NOT disappoint!!!! The proximity to Louisville is awesome, but there are also so many great little restaurants right there in Jeffersonville. This home was probably the best part of the trip though. It ended up being a little too chilly for us to take advantage of all the cool outside activities (ping pong, volleyball, you...
RIVERFRONT - Boat Slips - 10 Min to Dtown Lville

Historic Home in Old Louisville with deck and courtyard

10.0 out of 10, Exceptional, (42)
"While the property has a funky layout, it worked great for us. It is well supplied and stocked and is in a good location a short ride from Downtown and the 4th Street Live venues. Thanks Annie for the great stay!"
The price is AU$780
includes taxes & fees
3 Dec - 4 Dec
Historic Home in Old Louisville with deck and courtyard

***Oak Street Charm*** -EXPO, Downtown, casual luxury in historic Old Louisville

10.0 out of 10, Exceptional, (49)
"House was beatiful with plenty of room. James was awesome and reponded "
The price is AU$745
includes taxes & fees
23 Dec - 24 Dec
***Oak Street Charm*** -EXPO, Downtown, casual luxury in historic Old 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

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

8.8 out of 10, Excellent, (18)
"I stayed here for Ironman 70.3 Louisville. It was only 12 minutes from down town and the neighborhood was super quiet. Overall great location. "
The price is AU$584
includes taxes & fees
2 Dec - 3 Dec
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

9.6 out of 10, Exceptional, (62)
"We loved this cute and inviting home on a quiet street. The super private backyard with hot tub, patio, and sauna was like a private retreat. The large dining rm /living rm /kitchen was a great community space for our family gathering."
The price is AU$439
includes taxes & fees
2 Dec - 3 Dec
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

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

10.0 out of 10, Exceptional, (136)
"We were only in the home one night but everything was clean and comfortable. Great location, in walking distance to restaurants. Easy check in and fast communication from the host. Would stay there again."
The price is AU$610
includes taxes & fees
24 Dec - 25 Dec
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

Luxurious 2BR /2Bath with Outdoor Courtyard and Garage in Downtown Bardstown

10.0 out of 10, Exceptional, (210)
"Lovely house in the heart of bourbon country. Plenty of places within walking distance to eat. Short drive to many distilleries. Highly recommend!"
The price is AU$706
includes taxes & fees
3 Dec - 4 Dec
Luxurious 2BR /2Bath with Outdoor Courtyard and Garage in Downtown Bardstown

Stay at Whiskey Stop for Bourbon Trail! UL Games, KY Derby! Private Parking pad!

10.0 out of 10, Exceptional, (50)
"Great location! Clean, cozy, quiet and convenient. "
The price is AU$284
includes taxes & fees
2 Dec - 3 Dec
Stay at Whiskey Stop for Bourbon Trail! UL Games, KY Derby! Private Parking pad!

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

9.8 out of 10, Exceptional, (9)
"Comfy"
The price is AU$280
includes taxes & fees
2 Dec - 3 Dec
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

River City Retreat

9.8 out of 10, Exceptional, (6)
"Booked this house for a weekend golf trip with the guys. Location was great, a few minutes walk from downtown Jeffersonville. Check in was easy, they even accommodated us to check in early with flight schedules. There wasn’t any information on what needed to be done prior to check out - we ran the dishwasher, and gathered used towels. Good short trip, would recommend. "
River City Retreat

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (182)
"Loved the neighborhood and the condo was great. Beds were very comfortable and the sound machine kept out any unwanted noise from the street. The pizza place close by had fantastic food and service. We have a large SUV and had no problems backing into parking space. All good, would highly recommend. "
The price is AU$312
includes taxes & fees
2 Dec - 3 Dec
Historic District Townhouse in City's BEST Location

The Trifecta in Old Louisville

10.0 out of 10, Exceptional, (107)
"Great stay, location and cleanliness"
The Trifecta in Old Louisville

Huge and Contemporary Norton Commons House!

9.8 out of 10, Exceptional, (33)
"The property is in a very nice neighborhood with plenty of nearby businesses. A well built home. When I had questions or issues the response was in minutes, and was taken care of. "
The price is AU$1,029
includes taxes & fees
2 Dec - 3 Dec
Huge and Contemporary Norton Commons House!

3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU

10.0 out of 10, Exceptional, (161)
"This property was perfect for our girl's trip. The location was perfect, close to everything we wanted to do, and the property manager was great to work with. "
The price is AU$643
includes taxes & fees
27 Dec - 28 Dec
3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU

Cozy Louisville Home w/ Spacious Yard & Parking

10.0 out of 10, Exceptional, (7)
"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

New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

9.6 out of 10, Exceptional, (17)
"Group of 8 in town for Bourbon Trail tours. Plenty of room for everyone. Large kitchen and living area for everyone to gather. Beds were comfortable and could not hear noise from other bedrooms. Could hear the train, but came prepared with ear plugs, thanks to other reviews. Not a huge deal, but a little inconvenient...not enough towels. One bath towel per person, no hand towels, less than one wash cloth per person, no towels for hot tub, and no kitchen towels or dish cloths. "
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

5BR Very Spacious Home! Perfect for Family!

8.6 out of 10, Excellent, (8)
"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."
5BR Very Spacious Home! Perfect for Family!

New Downtown Luxury Townhouse in Bourbon Country

10.0 out of 10, Exceptional, (35)
"We really enjoyed our stay. 5 star place. Very clean and comfortable. Location, parking and noise level were perfect. Well stocked beautiful house. Safe and secure location. I would highly recommend staying here."
The price is AU$466
includes taxes & fees
4 Dec - 5 Dec
New Downtown Luxury Townhouse in Bourbon Country
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!

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$688
includes taxes & fees
12 Dec - 13 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
13 Dec - 14 Dec
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.
Beautiful view of the beach with palm trees

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