Scottsburg Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Scottsburg

Relaxing 7- bedroom Retreat Center at Englishton Park. 250 acres, hiking trails

10.0 out of 10, Exceptional, (1)
"My partner and I hoped for a peaceful getaway to hike and chose this place. As soon as we drove in, it seemed like nothing we’d quite seen. It’s walled like a park with an expansive front yard area, but it’s private. There are really cute old buildings. It was like we had the place to ourselves. There’s a kitchen and plenty of room in the sleeping building. Things were really clean and nice with a coffee welcome tray. Took a walk up to a little lake, and then hiked into the woods -...
The price is NZ$1,369
includes taxes & fees
4 Aug - 5 Aug
Relaxing 7- bedroom Retreat Center at Englishton Park. 250 acres, hiking trails

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

9.8 out of 10, Exceptional, (30)
"Clean, comfortable home with everything needed for our stay. "
The price is NZ$404
includes taxes & fees
13 July - 14 July
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (86)
"My husband and our son stayed for two nights and had a great time! The cabin was clean and just overall really nice. The hot tub was fantastic! The owners were very communicative and responsive. Overall, this made for a perfect little getaway!"
Stoney Creek - Sit back and unwind

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (38)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (3)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

10.0 out of 10, Exceptional, (145)
"Our family had a spectacular stay at the Stone Creek. Our kids (7, 3, 2 yo) had a blast playing pingpong, board games, and hot tub. Place was clean and we felt home. We’ll definitely come back!"
The price is NZ$882
includes taxes & fees
5 July - 6 July
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.8 out of 10, Exceptional, (46)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

Historic woodside view suite 205, Historic woodside view suite 205

9.0 out of 10, Wonderful, (2)
"This was perfect for my daughter and I for a quick one-day softball tourney. The apartment is extremely clean, easy to find, and comfortable. "
The price is NZ$260
includes taxes & fees
4 Aug - 5 Aug
Historic woodside view suite 205, Historic woodside view suite 205

COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

9.8 out of 10, Exceptional, (15)
"We enjoyed our stay tremendously. The host is extremely kind and attentive. The accommodations and everything the property has to offer is remarkable. We will definitely be staying here again! "
The price is NZ$626
includes taxes & fees
10 July - 11 July
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

Emerald Lake Retreat Charlestown

10.0 out of 10, Exceptional, (1)
"Excellent communication, fast responses, very accommodating. The layout is fantastic with lots of open space, comfortable bedrooms, and excellent amenities. The backyard is absolutely huge, probably 3 acres or so. Would stay again for sure."
The price is NZ$699
includes taxes & fees
6 July - 7 July
Emerald Lake Retreat Charlestown

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

10.0 out of 10, Exceptional, (23)
"The place was very cute, clean, and comfortable. Great stay! Host was very responsive. "
The price is NZ$406
includes taxes & fees
17 July - 18 July
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

10.0 out of 10, Exceptional, (112)
"Loved this property!!! We would definitely stay again!"
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (41)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (5)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (46)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

10.0 out of 10, Exceptional, (44)
"We had a great stay and the communication was terrific. Thanks SW"
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

Cozy Country Cabin quiet country retreat

10.0 out of 10, Exceptional, (175)
"We very much enjoyed our stay at this cabin. "
The price is NZ$344
includes taxes & fees
7 July - 8 July
Cozy Country Cabin quiet country retreat

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (4)
"Riverside Retreat is a must stay! It is a great location and exactly as described. Highly recommend. We will be back!"
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

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

9.4 out of 10, Exceptional, (13)
"This home was clean, comfortable and a great place to stay for the weekend. We enjoyed it! "
The price is NZ$531
includes taxes & fees
7 July - 8 July
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (46)
"We loved the house!"
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC: This holiday home rental outside of Scottsburg offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Scottsburg?

Linza Graham Park and Beechwood Park are a couple of lovely local spots to get outside and enjoy nature. Scott County Fairgrounds and Scottsburg City Hall 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.