Shepardsville Holiday Rentals

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Holiday Rentals in Shepardsville

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

2.0 star property
9.8 out of 10, Exceptional, (10)
"Very clean and comfortable. Property owner communicated well, we will be back."
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

10.0 out of 10, Exceptional, (50)
"We really enjoyed out stay. Place is immaculate and comfortable. Loved the covered outside deck and so did our Scottie dog! Wish we could have stayed longer. Will definitely look forward to staying there again. Thank you Bob and Joanne!"
The price is AU$388
includes taxes & fees
4 Dec - 5 Dec
A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

10.0 out of 10, Exceptional, (166)
"We celebrated a birthday in this beautiful place! The hideaway cabin was the perfect size for us and it felt incredibly homey and cozy. The hot tub was perfect and we had an absolute blast. Couldn’t have had a better birthday weekend so close to home! The hosts were incredibly kind and informative and we had privacy and were completely relaxed the entire weekend! Highly recommend this property "
The price is AU$332
includes taxes & fees
1 Dec - 2 Dec
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Lovely Terre Haute Home w/ Private Yard & Hot Tub!

8.0 out of 10, Very good, (4)
"Traveled from Missouri to Indiana for the covered bridge festival with the girls. We had a great time. The house was clean, good neighborhood, easy check in and we loved the hot tub after walking around all day! Will definitely stay here again. "
Lovely Terre Haute Home w/ Private Yard & Hot Tub!

This home is located in beautiful Parke County, a rustic and charming setting.

10.0 out of 10, Exceptional, (78)
"Thank you for the beautiful stay!! "
This home is located in beautiful Parke County, a rustic and charming setting.

Creekside cottage with hot tub and fishing

10.0 out of 10, Exceptional, (7)
"We were very pleased with everything at the Creekside Cottage. It was the perfect place and location. We especially enjoyed the hot tub at night."
Creekside cottage with hot tub and fishing

The Getaway House with Hot Tub and Pool. Pet Friendly

9.4 out of 10, Exceptional, (9)
"Excellent appreciated the check in and refresh of linens. House was clean and inviting "
The Getaway House with Hot Tub and Pool. Pet Friendly

The Rosedale House

2.0 star property
10.0 out of 10, Exceptional, (2)
"Brian was great at quickly responding to questions. House just as advertised. Very clean. Hot tub and fire pit with wood available but we didn’t use. (May want to add night stand lamps in bedrooms and reading light in living room, as there is mostly just ceiling lights) very close to Bridgeton, primary location of Covered Bridge Festival. "
The price is AU$453
includes taxes & fees
5 Dec - 6 Dec
The Rosedale House

Your One Of A Kind Rental! Family and Friendly With A Pool and Foosball Table.

10.0 out of 10, Exceptional, (3)
"Nice house well accommodated "
Your One Of A Kind Rental! Family and Friendly With A Pool and Foosball Table.

Great Weekend Getaway! Renovated in 2023, Zero Contact Booking, Pool Table, Wifi

9.2 out of 10, Wonderful, (26)
"The property was nice. The main house was nearby but we still felt we had privacy. The location was good. Not a busy area. Bedrooms were in the back which is nice if not everyone goes to bed at the same time. It suited our needs. Cute place."
Great Weekend Getaway! Renovated in 2023, Zero Contact Booking, Pool Table, Wifi

The Adams House 915

8.6 out of 10, Excellent, (7)
"We loved sitting outside on the large front porch. Communication with the property manager was excellent. This property was very close to Rose-Hulman and ISU. This is by no means a large property but inside you had everything you needed and the large covered front porch was an excellent addition to the property. We would stay again."
The price is AU$403
includes taxes & fees
27 Nov - 28 Nov
The Adams House 915

Home in Brazil

10.0 out of 10, Exceptional, (8)
"Clean and comfortable, great communication with owner "
The price is AU$182
includes taxes & fees
5 Dec - 6 Dec
Home in Brazil

Lakefront Paradise *Indoor Pool* *Arcade*

10.0 out of 10, Exceptional, (5)
"This lake house was a great stay. Our family had a great time swimming and playing games in the house. A perfect platform for a relaxing weekend. "
The price is AU$2,135
includes taxes & fees
8 Dec - 9 Dec
Lakefront Paradise *Indoor Pool* *Arcade*

911 N. 8th St. Your Home away from Home

8.0 out of 10, Very good, (7)
"Our stay was Awesome!!! It was so Homey and perfect for a weekend trip! Well furnished, great decor and Cool area minutes aways from lots of places too! as the terminator said "I'LL BE BACK""
The price is AU$305
includes taxes & fees
1 Dec - 2 Dec
911 N. 8th St. Your Home away from Home

Beach house on a lake

9.8 out of 10, Exceptional, (8)
"We enjoyed our stay. It was as described. We enjoyed playing pool and some board games. Only downside is there are no apps on the tv in the front bedroom. But that’s really a big deal. We would stay here again. "
Beach house on a lake

Tangerine Tranquility: 2BR*Grill* By ISU & Stadium

10.0 out of 10, Exceptional, (4)
"There was a little miss communication at check in! However that was quuickky resolved. Very convenient to the College as well as lots of restaurants. Enjoyed our visit!"
The price is AU$591
includes taxes & fees
30 Nov - 1 Dec
Tangerine Tranquility: 2BR*Grill* By ISU & Stadium

Vintage beauty - minutes to downtown, ISU campus and more. Pet Friendly!

The price is AU$518
includes taxes & fees
5 Dec - 6 Dec
Vintage beauty - minutes to downtown, ISU campus and more. Pet Friendly!

Modern 3-bed farmhouse AC, Wifi

10.0 out of 10, Exceptional, (4)
"Home was very clean, comfortable, and felt brand new! I'll be back! "
Modern 3-bed farmhouse AC, Wifi

Charming Terre Haute Retreat - Centrally located & Pet Friendly!

9.0 out of 10, Wonderful, (2)
"The property is great location to pretty much anything in Terre Haute. The owners pretty much supply everything you could possibly need and the place was neat and tidy. I loved the fact that the house was old but new. It was redone but they kept its original beauty. I loved everything about it . Had to give it a 4 overall because the listing said 3 bedrooms and there are only 2. The basement has a trundle bed though. Overall, super stay and convenient location. Thanks Lauren. I'd stay again!!"
The price is AU$482
includes taxes & fees
8 Dec - 9 Dec
Charming Terre Haute Retreat - Centrally located & Pet Friendly!

The Lighthouse- A Beautiful and Luxurious SmartHome.

9.6 out of 10, Exceptional, (5)
"Our family stayed here over the weekend to watch an Indiana State University football game. The neighborhood was really cute, and the house was close to the football stadium as well as a Walmart. The house was very clean and well organized and there was lots of room to relax, eat and catch-up after the football game. “Hey Google” kept us entertained as we asked lots of questions and changed the light colors in the rooms multiple times. Brandon was quite responsive and worked with us for a late...
The Lighthouse- A Beautiful and Luxurious SmartHome.
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 Shepardsville you may be interested in

La Quinta Inn & Suites by Wyndham Terre Haute

2.5 star property
8.8 out of 10, Excellent, (1010)
"Na"
The price is AU$159
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Terre Haute

Drury Inn & Suites Terre Haute

3.0 star property
9.4 out of 10, Exceptional, (1009)
"One of the best included breakfasts I have seen in many travels."
The price is AU$167
includes taxes & fees
24 Dec - 25 Dec
Drury Inn & Suites Terre Haute

Sleep Inn Terre Haute University Area

2.5 star property
7.8 out of 10, Good, (806)
"Staff was super friendly and helpful"
The price is AU$98
includes taxes & fees
24 Dec - 25 Dec
Sleep Inn Terre Haute University Area
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

Black Friday: Members save 30%+

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

Frequently asked questions

Are there holiday rentals in Shepardsville?

Yes, there are holiday rentals close to the most popular sights in Shepardsville, or you can select a more secluded option if you're looking for a relaxing stay.

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

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.: This holiday home rental outside of Shepardsville is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Shepardsville?

Explore the area and family-friendly sights such as Wabash Valley Family Sports Center, or get out into nature at a spot like Speed Beach. In the wider area, you’ll find Indiana State University and Rose-Hulman Institute of Technology.

What are holiday rentals like in Shepardsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shepardsville. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip.