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

Holiday Homes in Scottsburg

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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 homes

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 covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

2. 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
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 living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

5. 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
20 Oct - 21 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Room

6. 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 kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

7. 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 modern kitchen with a central island, black cabinets, a microwave, and a stove.

8. 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 wooden cabin with a porch, a staircase, and a deck.

9. 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 brick building with a central entrance, a small porch, and a pathway leading to the entrance.

10. 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 covered porch with a wooden door, potted plants, and a metal railing.

11. 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$371
includes taxes & fees
25 Oct - 26 Oct
The Artist’s A-Frame
A covered outdoor deck with a table and chairs, a ceiling fan, and a view of a body of water.

12. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (13 reviews)
"Located in a quiet area with great river views. Well stocked kitchen. Would stay there again"
United States
Phil T.
The price is AU$590
includes taxes & fees
2 Nov - 3 Nov
T&E Riverhouse Retreat
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

13. Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (77 reviews)
"Love the stay very relaxed"
United States
Steve C.
The price is AU$331
includes taxes & fees
20 Oct - 21 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A residential property with a red door, a small front yard with grass and shrubs, and a neighboring church with a steeple.

14. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
United States
Leslie W.
The price is AU$364
includes taxes & fees
20 Oct - 21 Oct
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
An aerial view of a swimming pool complex with multiple water slides and a surrounding area with lounge chairs and umbrellas.

15. #207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (46 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is AU$690
includes taxes & fees
12 Oct - 13 Oct
#207 King Suites, River Views, Deck, Downtown
An outdoor patio with a hot tub, a fire pit, and string lights.

16. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison Historic District
10.0 out of 10, Exceptional, (22 reviews)
"we had a good time. enjoyed our visit"
United States
Douglas S.
The price is AU$582
includes taxes & fees
7 Oct - 8 Oct
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
A hallway with a wooden floor, a brick wall, and a door with a window.

17. 604 GQ on Mulberry: 2 King Luxury Suites, Patio

604 GQ on Mulberry: 2 King Luxury Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
The price is AU$470
includes taxes & fees
12 Oct - 13 Oct
604 GQ on Mulberry: 2 King Luxury Suites, Patio
A spacious living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of a lake.

18. The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
Prospect
9.8 out of 10, Exceptional, (10 reviews)
"My family and I had a wonderful trip. The house was absolutely beautiful. Everything was clean and well taken care of we couldn’t have asked for a better vacation"
United States
Thomas c.
The price is AU$855
includes taxes & fees
7 Oct - 8 Oct
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
An outdoor patio with a hot tub, a fire pit, and string lights.

19. "Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
Madison Historic District
9.8 out of 10, Exceptional, (17 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is AU$544
includes taxes & fees
14 Oct - 15 Oct
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
A wooden swing bed with a pergola roof, string lights, and a wooden deck.

20. King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Jeffersonville
9.6 out of 10, Exceptional, (17 reviews)
"The property was very nice for our family getaway, would book again."
United States
Roberta
The price is AU$546
includes taxes & fees
13 Oct - 14 Oct
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
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

Scottsburg Holiday Homes information

Number of reviews
398
Accommodation
94 Holiday Homes
Lowest Price
AU$241
Highest Price
AU$855