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Compare 88 Vacation Homes in Scottsburg with updated reviews, rates, and availability.

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

9.8 out of 10, Exceptional, (39)
"The space was perfect for 4 of us traveling for a girls’ trip. Location was close to all the shops and restaurants. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

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

9.8 out of 10, Exceptional, (26)
"We stayed in this property on our annual Madison visit. It had everything we needed and was very comfortable and clean. We would stay here again."
The price is SAR 375
SAR 811 total
includes taxes & fees
13 Mar - 14 Mar
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

10.0 out of 10, Exceptional, (15)
"We had a great time, the house was perfect."
The price is SAR 484
SAR 1,005 total
includes taxes & fees
16 Mar - 17 Mar
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

10.0 out of 10, Exceptional, (42)
"The house is stunning. Very well decorated and completely outfitted for our stay. The kitchen had everything you could need. The owners were easy to communicate with and very helpful. Would highly recommended the property. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

Evergreen: Work Friendly & Near Downtown

9.0 out of 10, Wonderful, (13)
"This was a wonderful place for our family of five to stay! The beds were comfortable, the house was clean, and the kitchen was well stocked, so we could cook a large breakfast for all of us. The neighborhood was quiet, and it was a nice place for us to walk our dogs. I would highly recommend it, and we plan to stay there again when we’re back in Louisville. "
Evergreen: Work Friendly & Near Downtown

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

9.8 out of 10, Exceptional, (42)
"Charming little house in Madison, with good access to downtown. We had a great day exploring the shops and the winery and it was nice to come back to a snug little space. We did not have trouble with noise from the saloon but it seemed pretty low key despite a party weekend. Hosts had clear communication with us."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

9.4 out of 10, Exceptional, (15)
"Very nice home with lots of space and great location to many shops."
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (19)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
Family/Pet-Friendly Riverside Home w/Amazing Views

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10.0 out of 10, Exceptional, (30)
"Everything was just as described! "
10 Min to Louisville, Huge Hot Tub, Awesome Backyard

The Artist’s A-Frame

10.0 out of 10, Exceptional, (11)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is SAR 435
SAR 867 total
includes taxes & fees
13 Mar - 14 Mar
The Artist’s A-Frame

Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

10.0 out of 10, Exceptional, (24)
"This was a wonderful place for our weekend in Madison. We walked everywhere we wanted to go. The house is very clean and updated with everything we needed. We really appreciated having large beds and bathrooms for each bedroom. "
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

Spacious Louisville Ohio riverfront retreat with gorgeous view.

10.0 out of 10, Exceptional, (143)
"We were in town for a family wedding and rented this home for an extended weekend. The setting on the river was wonderful, as were the views from the common area of the house. The kitchen/dining/family room area were perfect for 9 people, and the shuffleboard was an especially big hit. There was an abundance of comfortable seating, including four recliners. We also appreciated the numerous amenities including a great coffee bar. We'd certainly consider renting this house again if needing a...
Spacious Louisville Ohio riverfront retreat with gorgeous view.

Red comfy cottage

10.0 out of 10, Exceptional, (70)
"House was in great condition and had everything we needed. We came for a girls trip to hike Clifty Falls and go shopping around downtown. Would stay again. "
Red comfy cottage

Cozy home located close to Louisville that features 2 separate living areas.

10.0 out of 10, Exceptional, (4)
"Loved the number of bedrooms, both upstairs (with kitchenette) and on the first floor, great options. Host very responsive to any questions providing great help when needed for 80+ year old Mom and sister on crutches. Would recommend this home to anyone! A little outside New Albany in Greenville, IN, but close to shops. Thanks to the hosts!"
The price is SAR 176
SAR 920 total
includes taxes & fees
8 Apr - 9 Apr
Cozy home located close to Louisville that features 2 separate living areas.

Cozy family home. 19 minutes from Churchill Downs

9.4 out of 10, Exceptional, (23)
"Plenty of room , three bathrooms and three nice beds"
Cozy family home. 19 minutes from Churchill Downs

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

9.4 out of 10, Exceptional, (10)
"This home was clean, comfortable and a great place to stay for the weekend. We enjoyed it! "
The price is SAR 375
SAR 1,076 total
includes taxes & fees
17 Mar - 18 Mar
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

Relaxing Country Getaway

9.6 out of 10, Exceptional, (29)
"We enjoyed our stay and would definitely stay here again. It was very clean and comfortable. A few of the downsides to be aware of:The furnace ran constantly bc the cottage is not insulated so it had to constantly run to keep us warm. If you’re staying here during the winter months, I would suggest sleeping in the back bedroom, so you don’t have to hear it running.The kitchen did not have steak knives or a butcher knife and cutting board, so bring your own stuff if you're going to grill a...
Relaxing Country Getaway

Bungalow on Main!!

9.6 out of 10, Exceptional, (8)
"We had a great weekend. The house was perfect for the four of us. Plenty of room and great space to gather, eat, play a game, watch a movie, just enjoy each other. "
Bungalow on Main!!

Work&Play: Work Friendly, Ping Pong, & Grill

8.6 out of 10, Excellent, (14)
"Nice quiet neighborhood and location. Very convenient to retail stores and wide selection of restaurants. Unfortunately, two of three bathtubs did not drain properly. Tub in basement did not drain at all and was unusable. One upstairs tub stopped up with hair clog that we cleaned out ourself. "
Work&Play: Work Friendly, Ping Pong, & Grill

NEW Fire Pit Area\Lrg Fenced Backyard\Master with King\Discovery Play-set

10.0 out of 10, Exceptional, (7)
"This house was everything it was advertised to be! All the furniture was comfortable and clean! Everything you need has been thought of. Would definitely rent again"
The price is SAR 571
SAR 1,446 total
includes taxes & fees
19 Mar - 20 Mar
NEW Fire Pit Area\Lrg Fenced Backyard\Master with King\Discovery Play-set
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 property types 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 SAR 1,500
SAR 3,121 total
includes taxes & fees
17 Mar - 18 Mar
Relaxing 7- bedroom Retreat Center at Englishton Park. 250 acres, hiking trails

stayAPT Suites Louisville North-Clarksville

4.0 star property
9.8 out of 10, Exceptional, (37)
"Property was very nice and accommodating for what we needed. Close to shopping and several restaurants. Rooms were large and equipped for cooking. Liked having the living quarters and bedroom separated. I would recommend this property and will stay again when in the area! "
The price is SAR 446
SAR 504 total
includes taxes & fees
13 Mar - 14 Mar
stayAPT Suites Louisville North-Clarksville

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (19)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
Family/Pet-Friendly Riverside Home w/Amazing Views
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.