Photo by Jim Watkins

Jackson County 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

Top Holiday Rentals Destinations in Jackson County

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

2.0 star property
10.0 out of 10, Exceptional, (10)
"Wonderful Host and property."
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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

10.0 out of 10, Exceptional, (23)
"The house was great! Easy to find, quiet area, great fenced in backyard, very clean place. We were glad to find it while in town for just a night."
The price is NZ$406
includes taxes & fees
17 July - 18 July
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The price is NZ$747
includes taxes & fees
16 July - 17 July
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Charming Historic Retreat Home

10.0 out of 10, Exceptional, (12)
"Beautiful town with an abundance of nature close by."
The price is NZ$382
includes taxes & fees
16 July - 17 July
Charming Historic Retreat Home

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

10.0 out of 10, Exceptional, (23)
"We needed a place to stay halfway-ish between Tennessee and Chicago, and this was a nice, clean place that totally fulfilled our needs."
Country home with beautiful views and access to hiking, biking, and horse trails

Robin's Egg ~ Private Downtown, Pet-Friendly Gem

9.4 out of 10, Exceptional, (3)
"Nice older house in a really cool neighborhood. Host was great and easy to reach and always got right back in touch. "
The price is NZ$501
includes taxes & fees
13 July - 14 July
Robin's Egg ~ Private Downtown, Pet-Friendly Gem

Walkable Downtown Getaway (FREE Bikes to use)

10.0 out of 10, Exceptional, (1)
"Very nice location and studio with all accommodations "
The price is NZ$300
includes taxes & fees
9 July - 10 July
Walkable Downtown Getaway (FREE Bikes to use)

J & N Spacious & Cozy Home, Columbus Indiana

10.0 out of 10, Exceptional, (18)
"We greatly enjoyed our stay in this wonderful home! The backyard was a great place to hang out and watch the squirrels, rabbits and birds! We would definitely stay here again!"
The price is NZ$1,034
includes taxes & fees
29 July - 30 July
J & N Spacious & Cozy Home, Columbus Indiana

4 Paws Getaway in Brown County

9.8 out of 10, Exceptional, (67)
"I cannot say enough good things about this house! Every single detail has been thought of. The house was immaculately clean, gorgeously decorated and very spacious. This was the perfect place for our family to celebrate my daughter’s graduation from IU. "
4 Paws Getaway in Brown County

Charming 2-bedroom house in perfect Nashville! Close to town

10.0 out of 10, Exceptional, (11)
"Fantastic accommodations and hosts. "
The price is NZ$539
includes taxes & fees
6 July - 7 July
Charming 2-bedroom house in perfect Nashville! Close to town

Story Time Retreat in Brown County

2.0 star property
10.0 out of 10, Exceptional, (5)
"Story Time Retreat was truly that. Our family spent Thanksgiving here and it was a joyful experience. The property was very clean and well appointed. Our host Marisa thought of everything. She thoughtfully provided a scrumptious pumpkin roll for us to enjoy and the coffee bar was outstanding. The kitchen was amazing too and had all we needed to cook a fabulous Thanksgiving feast! Most of all, we enjoyed the serenity and quietude this property provided. It was just what we needed. We highly...
Story Time Retreat in Brown County

Cozy 2-bedroom RV with WiFi, AC Red Barn music Venue Camp ground

10.0 out of 10, Exceptional, (1)
"Great location ! Great Host"
The price is NZ$408
includes taxes & fees
9 July - 10 July
Cozy 2-bedroom RV with WiFi, AC Red Barn music Venue Camp ground

Charming bungalow with a hot tub, walking distance to downtown Nashville

9.6 out of 10, Exceptional, (65)
"This house is adorable, clean and very well designed. We enjoyed our stay and will book again!"
The price is NZ$569
includes taxes & fees
23 July - 24 July
Charming bungalow with a hot tub, walking distance to downtown Nashville

Creekside bungalow with a hot tub, walking distance to downtown Nashville

9.8 out of 10, Exceptional, (65)
"We loved our stay at The Bullfrog Bungalow and will definitely be back next year! "
The price is NZ$530
includes taxes & fees
7 July - 8 July
Creekside bungalow with a hot tub, walking distance to downtown Nashville

The Nest - Located in the Heart of Nashville Indiana!

9.8 out of 10, Exceptional, (161)
"The Nest was perfect. Very clean, comfortable and had everything we needed for a nice night away. "
The Nest - Located in the Heart of Nashville Indiana!

Suite in downtown Nashville

7.4 out of 10, Good, (14)
"Julie was great to work with! Had a great time and loved the location! "
Suite in downtown Nashville

Helmsburg Homestead Historic Log Cabin in Nashville Indiana

10.0 out of 10, Exceptional, (3)
"Had a wonderful girls trip!"
The price is NZ$1,000
includes taxes & fees
30 July - 31 July
Helmsburg Homestead Historic Log Cabin in Nashville Indiana

1 bdrm Modern Oasis near everything.

9.2 out of 10, Wonderful, (56)
"This is a very nice property. Convenient to o Downtown Nashville and easy to find. Enjoyed our stay. "
The price is NZ$397
includes taxes & fees
20 July - 21 July
1 bdrm Modern Oasis near everything.

Private 3.5 acre Waterfront Cabin with Hot Tub, WiFi, Minutes from Nashville

10.0 out of 10, Exceptional, (11)
The price is NZ$929
includes taxes & fees
15 July - 16 July
Private 3.5 acre Waterfront Cabin with Hot Tub, WiFi, Minutes from Nashville

Hidden Retreat on 30 Wooded Acres 5 Miles to Town

10.0 out of 10, Exceptional, (31)
"This modern, well-designed property is deep in the forest, with walking trails to enjoy. We only stayed one night en route to Chicago, but enjoyed the outdoors and slept like babies. Lovely."
The price is NZ$472
includes taxes & fees
6 July - 7 July
Hidden Retreat on 30 Wooded Acres 5 Miles to Town
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