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Compare 91 Vacation Homes in Scottsburg with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (32)
"We enjoyed our weekend in Madison! This property was clean and well managed, and in a great location. We were able to walk down to the river, and to the shopping district, spent the morning hiking in Clifty Falls, and shared a bottle of wine in the afternoon at the Thomas Family Winery. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (18)
"We stayed at the house for two nights while in town for a horse show. We had an amazing time and the house was perfect for us. The house had everything we needed and we really enjoyed the deck out back with the small fire pit and view of the river! Overall an awesome house. "
Family/Pet-Friendly Riverside Home w/Amazing Views

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (34)
"We had an amazing time in Madison! The home was spotless and had everything you will need plus more! Mona checks in to be sure everything is fine and suggested things to do. You will love the location! Will be my place to stay at all upcoming visits! "
The Wadsworth in National Historic District of Madison, Indiana.

Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

10.0 out of 10, Exceptional, (206)
"The house was very clean and decorated nicely. Beautiful old river town. Wifi was spotty. This was only an issue in the evening when we wanted to watch a movie. That's my only complaint and for sure not a deal breaker. Great property. Would stay here again!"
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

Evergreen: Work Friendly & Near Downtown

8.8 out of 10, Excellent, (11)
"We really enjoyed the house and it was comfortable for 5 adults. The location is very convienient to Louisville and to "hit" the Bourbon Trail. There are several nice restaurants and stores near the home which was very nice. We would stay again."
Evergreen: Work Friendly & Near Downtown

Country retreat in the city.

9.8 out of 10, Exceptional, (8)
"Very comfortable and clean. Would stay again "
The price is SAR 826
SAR 1,545 total
includes taxes & fees
29 Nov - 30 Nov
Country retreat in the city.

Red comfy cottage

10.0 out of 10, Exceptional, (69)
"The home was fabulously clean, relaxing, and perfect for our small family. The location is not ideal as it is located between the Comfort Inn and a vehicle repair shop and is on the corner of two very busy/noisy roads. The front yard is literally the driveway between the two so smaller kids would not be able to go from the car to the house without an adult. However, the backyard was very private and the hot tub was the key to a wonderfully relaxing weekend. "
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 282
SAR 1,086 total
includes taxes & fees
4 Dec - 5 Dec
Cozy home located close to Louisville that features 2 separate living areas.

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

9.6 out of 10, Exceptional, (13)
"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

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

10.0 out of 10, Exceptional, (20)
"We had a great stay in Madison. The town was very cute and most everything we wanted to do was within walking distance. The house was clean and well maintained. The only downside side was the fire place and washer were not in working condition during the time of our visit. "
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

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

10.0 out of 10, Exceptional, (17)
"Beds were comfortable, space was cozy, location ideal to everything. Wouldn’t hesitate to recommend to others and would stay again. Super helpful host! "
The price is SAR 394
SAR 816 total
includes taxes & fees
3 Dec - 4 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10.0 out of 10, Exceptional, (24)
"Overall it was great. Everyone enjoyed it."
10 Min to Louisville, Huge Hot Tub, Awesome Backyard

Relaxing Country Getaway

9.6 out of 10, Exceptional, (25)
"What a beautiful spot! Secluded and wooded. Cozy and the hot tub hit the spot! 10 out of 10 would recommend. "
Relaxing Country Getaway

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

10.0 out of 10, Exceptional, (40)
"This is a beautiful house and very well equipped. Alert - all the bedrooms are on the 2nd floor with is up 25 steps - straight up! The 2 bathrooms on the 2nd floor are not connected to any of the bedrooms and are right next to each other. So - unusual. Wonderful location- easy party - comfortable beds. We did put some of the breakable decorations in a safer place because of our little ones. We enjoyed our stay and would recommend this home. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (27)
"Great location! Fabulous place to stay! Very clean with comforts of home. Walked to all our destinations during our 3 day visit."
The price is SAR 1,164
SAR 2,161 total
includes taxes & fees
1 Dec - 2 Dec
#207 King Suites, River Views, Deck, Downtown

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

10.0 out of 10, Exceptional, (17)
"We had a short stay to visit some distilleries on our way to the Smokies. It was a clean, quiet, beautiful stay in the country. The only thing I would mention is the numerous plug-ins were overwhelming to the point that we unplugged them while there. Otherwise, great stay!"
The price is SAR 620
SAR 1,031 total
includes taxes & fees
2 Dec - 3 Dec
Country home with beautiful views and access to hiking, biking and horse trails.

Bungalow on Main!!

9.4 out of 10, Exceptional, (3)
"The house was great. Plenty of room for everyone to stretch out and have space (4 adults and a 3 year old). The owner was quick to respond to questions and allowed us to check in 2 hours early so we had time to freshen up before the rehearsal dinner. It was a great weekend!"
Bungalow on Main!!

"Madison Manor I" - HOT TUB - FIRE PIT - Holiday Specials!

9.2 out of 10, Wonderful, (7)
"Loved staying here! We brought 2 teenage girls who were easily entertained being close to Main St and shopping. The game room was great, and we all loved the hot tub. The home was so clean and organized. The house is quaint and cozy. We will definitely be back!"
The price is SAR 616
SAR 1,510 total
includes taxes & fees
1 Dec - 2 Dec
"Madison Manor I" - HOT TUB - FIRE PIT - Holiday Specials!

The Luxe! 3 bedroom 1 bath

9.6 out of 10, Exceptional, (8)
"The home is old and needs more work but it served its purpose for us to have a place to stay. It is definitely not "Luxe" as the title states. The kitchen was lacking basic cookware such as a frying pan for cooking breakfast. There are no dressers for clothes and minimal hangers in the closets forcing us to live out of our suitcase for the 6 nights we were there. If you need a place to sleep and shower and not much more, it's a good fit. If you want or need more, this is not the place for you. "
The Luxe! 3 bedroom 1 bath

The Grayson! Cozy 3bedroom 1bath home, 12 min from downtown Louisville!

9.2 out of 10, Wonderful, (5)
"We recently stayed at a home in New Albany for six nights, and overall, it was a decent experience. The house itself is nicely decorated and has a cozy feel, but it is on the smaller side and lacks a dedicated eating space for a family, which can make meals a bit challenging. There’s also no private parking, so you’ll need to park on the street, which might be something to keep in mind. Inside, the space is beautiful, but the beds weren’t the most comfortable; they felt a bit worn and seemed...
The Grayson! Cozy 3bedroom 1bath home, 12 min from downtown 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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Other property types in Scottsburg

7-bedroom vacation retreat 20 minutes from historic Madison Indiana

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 2,253
SAR 4,080 total
includes taxes & fees
3 Dec - 4 Dec
7-bedroom vacation retreat 20 minutes from historic Madison Indiana

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (18)
"We stayed at the house for two nights while in town for a horse show. We had an amazing time and the house was perfect for us. The house had everything we needed and we really enjoyed the deck out back with the small fire pit and view of the river! Overall an awesome house. "
Family/Pet-Friendly Riverside Home w/Amazing Views

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (34)
"We had an amazing time in Madison! The home was spotless and had everything you will need plus more! Mona checks in to be sure everything is fine and suggested things to do. You will love the location! Will be my place to stay at all upcoming visits! "
The Wadsworth in National Historic District of Madison, Indiana.
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.