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

Holiday Homes in Scottsburg

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 €184
includes taxes & fees
24 Oct - 25 Oct
Cozy Tiny House in Scottsburg
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

2. 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 €255
includes taxes & fees
28 Sept - 29 Sept
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.

3. 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 €147
includes taxes & fees
28 Sept - 29 Sept
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.

4. 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, (52 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 €221
includes taxes & fees
8 Oct - 9 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.

5. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.6 out of 10, Exceptional, (19 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.
Modern cabin very close to scenic riverfront walks
A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

6. 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 Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A covered porch with a wooden door, potted plants, and a metal railing.

7. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (40 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 €218
includes taxes & fees
29 Sept - 30 Sept
The Artist’s A-Frame
A wooden cabin with a porch, a staircase, and a deck.

8. 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 €152
includes taxes & fees
5 Oct - 6 Oct
Sassafras Woodland Cabin at Lost Trails
A kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

9. 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, (5 reviews)
"It was lovely!"
United States
Carolyne R.
The price is €413
includes taxes & fees
5 Oct - 6 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.

10. 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
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

11. 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, (76 reviews)
"Love the stay very relaxed"
United States
Steve C.
The price is €205
includes taxes & fees
1 Oct - 2 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
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.
T&E Riverhouse Retreat
A residential property with a red door, a small front yard with grass and shrubs, and a neighboring church with a steeple.

13. 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 €214
includes taxes & fees
4 Oct - 5 Oct
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

14. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Such a cute little place for my husband and I to get away for my birthday weekend! The house was adorable, well stocked for daily needs and very clean! Will definitely stay here again and recommend it to others!! "
United States
Claire S.
The price is €294
includes taxes & fees
30 Sept - 1 Oct
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
An outdoor patio with a hot tub, a fire pit, and string lights.

15. "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
9.6 out of 10, Exceptional, (15 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is €332
includes taxes & fees
5 Oct - 6 Oct
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
An outdoor patio with a hot tub, a fire pit, and string lights.

16. "Madison Manor II” Last Minute Chautauqua 1 Night Special! Hot Tub, Game Room

"Madison Manor II” Last Minute Chautauqua 1 Night Special! Hot Tub, Game Room
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 €338
includes taxes & fees
7 Oct - 8 Oct
"Madison Manor II” Last Minute Chautauqua 1 Night Special! Hot Tub, Game Room
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
604 GQ on Mulberry: 2 King Luxury Suites, Patio
An aerial view of a swimming pool complex with multiple water slides and a surrounding area with lounge chairs and umbrellas.

18. #207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (45 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 €403
includes taxes & fees
30 Sept - 1 Oct
#207 King Suites, River Views, Deck, Downtown
An aerial view of a water park with multiple swimming pools, slides, and a large blue spiral water feature.

19. #209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison Historic District
10.0 out of 10, Exceptional, (72 reviews)
"The house was clean, comfortable, and had everything we needed. The location was great; very close to restaurants and shops on Main Street as well as the parks by the river. "
United States
Hannah M.
#209 Kings, River View, Deck, Bicentennial Park
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 €348
includes taxes & fees
30 Sept - 1 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Scottsburg Hotel Reviews

HavenPointe Inn & Suites

HavenPointe Inn & Suites

8/10 Good
"The staff and room was wonderful. We had a great stay and plan to again. The only negatives was no place for hanging clothes and needed more towels, there were two of us and was only given 2 towels. I like a towels for my hair. Next time I’ll remember to bring my own hair towel"
Mecca 3-night trip
Posted 12 hours ago
HavenPointe Inn & Suites

Find out more about Scottsburg

Scottsburg Holiday Homes information

Number of reviews
444
Accommodation
92 Holiday Homes
Lowest Price
€147
Highest Price
€413