A serene lake at sunset with a reflection of the sky, surrounded by trees and vegetation.

Scottsburg Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Scottsburg holiday rentals

A covered patio with a door, two wicker chairs, and string lights.

1. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is AU$292
includes taxes & fees
24 Oct - 25 Oct
Cozy Tiny House in Scottsburg
A room with a bed, two armchairs, a small table, and a microwave.

2. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is AU$443
includes taxes & fees
7 Oct - 8 Oct
Lakeside Cottage: 1 bed/1 bath
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

3. Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (43 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is AU$411
includes taxes & fees
17 Oct - 18 Oct
Country home with beautiful views and access to hiking, biking, and horse trails
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

4. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (25 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is AU$241
includes taxes & fees
20 Oct - 21 Oct
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

5. Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Memphis
10.0 out of 10, Exceptional, (27 reviews)
"Great host and a great location!"
United States
P a.
The price is AU$244
includes taxes & fees
29 Oct - 30 Oct
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

6. The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (53 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
The price is AU$384
includes taxes & fees
18 Oct - 19 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

7. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is AU$286
includes taxes & fees
12 Oct - 13 Oct
Modern cabin very close to scenic riverfront walks
Room

8. Country living minutes away from Churchill Downs, Airport, major attractions.

Country living minutes away from Churchill Downs, Airport, major attractions.
Charlestown
9.6 out of 10, Exceptional, (7 reviews)
"So glad we went here for our mini getaway! Definitely a unique place to stay. Room was great and we got to tour other areas in and around the castle. David is a great host and we enjoyed talking with him! Going to try and make it back up for the festival this fall."
United States
Cari H.
The price is AU$280
includes taxes & fees
28 Oct - 29 Oct
Country living minutes away from Churchill Downs, Airport, major attractions.
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

9. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is AU$184
includes taxes & fees
7 Oct - 8 Oct
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A log cabin with a fire pit and outdoor seating.

10. Family-friendly cabin with game room and backyard!

Family-friendly cabin with game room and backyard!
Hanover
10.0 out of 10, Exceptional, (4 reviews)
"Host is very easy to communicate with and the property provided us with great memories! Would definitely stay here again!"
United States
Eli H.
The price is AU$605
includes taxes & fees
4 Nov - 5 Nov
Family-friendly cabin with game room and backyard!
A kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

11. The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.2 out of 10, Wonderful, (7 reviews)
"It was lovely!"
United States
Carolyne R.
The price is AU$675
includes taxes & fees
18 Oct - 19 Oct
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

12. The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Salem
9.6 out of 10, Exceptional, (9 reviews)
"We really enjoyed our stay at the Lanning house. It was a very clean and comfortable place to stay. We enjoyed the history of the home as well."
United States
Andrew H.
The price is AU$454
includes taxes & fees
12 Oct - 13 Oct
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

13. The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (51 reviews)
"Had a very nice stay"
United States
Brad P.
The price is AU$329
includes taxes & fees
7 Oct - 8 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Property grounds

14. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is AU$251
includes taxes & fees
12 Oct - 13 Oct
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A modern kitchen with a central island, black cabinets, a microwave, and a stove.

15. Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Vallonia
10.0 out of 10, Exceptional, (18 reviews)
"Outstanding place to stay. Plenty of peace and quiet but still not too far from groceries and gas."
United States
James
The price is AU$487
includes taxes & fees
13 Oct - 14 Oct
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A house with a large garage, a dock, and a river.

16. River Retreat

River Retreat
Charlestown
10.0 out of 10, Exceptional, (1 review)
"Easy check in. Nice cozy home right by the river. Even left a golf cart for use when staying!"
United States
Brady S.
The price is AU$413
includes taxes & fees
14 Oct - 15 Oct
River Retreat
A covered porch with a wooden door, potted plants, and a metal railing.

17. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (41 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is AU$374
includes taxes & fees
3 Nov - 4 Nov
The Artist’s A-Frame
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18. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is AU$252
includes taxes & fees
7 Oct - 8 Oct
Maple Cozy Cabin at Lost Trails
A wooden cabin with a porch, a staircase, and a deck.

19. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AU$248
includes taxes & fees
12 Oct - 13 Oct
Sassafras Woodland Cabin at Lost Trails
A white bedroom with a large bed, a wooden nightstand, and a wall-mounted lamp.

20. Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
The price is AU$1,678
includes taxes & fees
3 Nov - 4 Nov
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
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 Scottsburg Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"The experience we had at this motel was great staff was friendly and helpful room was clean and organized. We will be staying at hill side again in the future"
William 1-night trip
Posted 1 day ago
Hillside Inn

Find out more about Scottsburg

Everything you need to know about Scottsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Scottsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Scottsburg holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Scottsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Scottsburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Scottsburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Scottsburg holiday rentals we have selected for you start as low as AU$184 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Scottsburg rentals

At Expedia, we put the best Scottsburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Scottsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Scottsburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Scottsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Scottsburg?

Yes, there are holiday rentals in Scottsburg close to Scott County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Scottsburg is known for its monuments and entertainment choices. Make sure you have time to check out the theatres and churches during your trip.

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

Cozy Tiny House in Scottsburg: This highly rated holiday home rental in Scottsburg is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Scottsburg?

Beechwood Park and Lake Iola Park are a couple of lovely local spots to get outside and enjoy nature. Westwood Golf Course and Hardy Lake are other places to visit while you're in town.

What are holiday rentals like in Scottsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Scottsburg. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.