Holiday Rentals in Scottsburg

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Our top choices for Scottsburg holiday rentals

Holiday Home in Scottsburg

Cozy Tiny House in Scottsburg
9.6 out of 10, Exceptional, (4)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is €154
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg
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 -...
United States
T D.
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails
9.8 out of 10, Exceptional, (16)
"Loved everything about the place the lake was great. Wish the play house was air conditioned cause it get hot even with the fan but was amazing will stay again"
United States
Christine w.
The price is €310
includes taxes & fees
23 Jan - 24 Jan 2026
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW
4.0 star property
9.8 out of 10, Exceptional, (43)
"Excellent stay. One of my favorite hotels in the area. They never disappoint "
United States
Julia
The price is €143
includes taxes & fees
29 Dec - 30 Dec
stayAPT Suites Louisville North-Clarksville
10.0 out of 10, Exceptional, (14)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is €258
includes taxes & fees
30 Dec - 31 Dec
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is €167
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Country Cabin quiet country retreat
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
9.8 out of 10, Exceptional, (62)
"Host was responsive to all messages. The small home we stayed in was so cozy and clean. Directions on how to get there were clear and easy to follow. 10/10 would recommend."
United States
Haley V.
The price is €200
includes taxes & fees
29 Dec - 30 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
4.0 star property
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
United States
Tammy
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Holiday Home in Madison

The Artist’s A-Frame
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is €195
includes taxes & fees
4 Jan - 5 Jan 2026
The Artist’s A-Frame
10.0 out of 10, Exceptional, (14)
"Property was very clean, smelt great, and spacious. Located in a nice neighborhood. Hosts were extremely accommodating and friendly. Would definitely stay here again if I'm back in the area for an overnight trip. "
United States
Mandy M.
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
10.0 out of 10, Exceptional, (30)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is €219
includes taxes & fees
30 Dec - 31 Dec
Country home with beautiful views and access to hiking, biking, and horse trails
9.8 out of 10, Exceptional, (53)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is €194
includes taxes & fees
2 Jan - 3 Jan 2026
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.2 out of 10, Wonderful, (5)
"The property is very spacious, private and on a beautiful lot. We did have concerns, however, on the upkeep. The home could use some TLC. All it would take would be a good thorough cleaning, a couple more window drapes and lighting. We have brought this to the attention of the property manager and hopefully the issues will be addressed. There is so much potential and enough gathering space for larger groups.Just a short drive to Madison and Clifty Falls. Great location."
United States
Debbie K.
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Holiday Home in Charlestown

Emerald Lake Retreat Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is €398
includes taxes & fees
30 Dec - 31 Dec
Emerald Lake Retreat Charlestown
10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is €129
includes taxes & fees
10 Jan - 11 Jan 2026
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
9.8 out of 10, Exceptional, (37)
"Great place to stay for Hanover college "
United States
Lindsey M.
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
2.0 star property
The price is €110
includes taxes & fees
5 Jan - 6 Jan 2026
The Madison Inn, Est 1925 Historic suite 107
10.0 out of 10, Exceptional, (62)
"Great house, great location and the host was very responsive! I would definitely recommend this place. "
United States
Lisa C.
#209 Kings, River View, Deck, Bicentennial Park
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

Find out more about Scottsburg

Everything you need to know about Scottsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Scottsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Scottsburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Scottsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Scottsburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Scottsburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Scottsburg holiday rentals we have selected for you start as low as €143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Scottsburg rentals

At Expedia, we put the best Scottsburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Scottsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Scottsburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Scottsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails: This highly rated holiday home rental in Scottsburg is located on a lake, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Scottsburg?

Pigeon Roost Memorial and Hardy Lake are a couple of lovely local spots to get outside and enjoy nature. Scott County Fairgrounds and Westwood Golf Course 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.