Photo by Susan Ross

Jennings County Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Featured Jennings County Holiday Rentals

Property grounds
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

North Vernon
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 HK$1,927
HK$2,515 total
includes taxes & fees
11 Dec - 12 Dec
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW
Fridge, microwave, oven, stovetop
Charming Historic Retreat Home

Charming Historic Retreat Home

Vernon
10.0 out of 10, Exceptional, (18)
"Perfect location for my visit with family!"
United States
Christine R.
The price is HK$1,168
HK$1,988 total
includes taxes & fees
8 Dec - 9 Dec
Charming Historic Retreat Home
Exterior
Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy

2.0 star property
Columbus
9.4 out of 10, Exceptional, (55)
"It was amazing stay!"
United States
Anas
The price is HK$693
HK$1,155 total
includes taxes & fees
8 Dec - 9 Dec
Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy
Exterior
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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

2.0 star property
Vallonia
10.0 out of 10, Exceptional, (13)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is HK$1,366
HK$2,315 total
includes taxes & fees
8 Dec - 9 Dec
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
1 bedroom, desk, WiFi, bed sheets
East Main Lofts - Coastal 201

East Main Lofts - Coastal 201

Madison
9.8 out of 10, Exceptional, (9)
"This was a perfect spot for us for a long weekend stay. The place was very clean and the host had great instructions/recommendations etc. "
United States
Missy R.
The price is HK$1,946
HK$3,250 total
includes taxes & fees
8 Dec - 9 Dec
East Main Lofts - Coastal 201
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Madison
10.0 out of 10, Exceptional, (12)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is HK$1,183
HK$2,811 total
includes taxes & fees
8 Dec - 9 Dec
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

Madison
9.8 out of 10, Exceptional, (51)
"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 HK$973
HK$1,943 total
includes taxes & fees
8 Dec - 9 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

2.0 star property
Madison
The price is HK$617
HK$1,246 total
includes taxes & fees
14 Dec - 15 Dec
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Outdoor spa tub
"Liv's Honeymoon Treehouse Suite" private luxurious hideaway with a hot tub!

"Liv's Honeymoon Treehouse Suite" private luxurious hideaway with a hot tub!

2.0 star property
Milroy
10.0 out of 10, Exceptional, (2)
"Absolutely loved our stay. My girlfriend and I spent the evening in the hot tub with steaks on the black stone which was really nice to have provided. Very comfortable space and a great get away! Highly recommend!"
United States
Aidan H.
The price is HK$3,824
HK$5,291 total
includes taxes & fees
8 Dec - 9 Dec
"Liv's Honeymoon Treehouse Suite" private luxurious hideaway with a hot tub!
Exterior
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Scottsburg
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is HK$615
HK$1,343 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg
Outdoor dining
NEW! Secluded retreat with private pool+chef's kitchen+hot tub+pond+theaterl!

NEW! Secluded retreat with private pool+chef's kitchen+hot tub+pond+theaterl!

2.0 star property
Freetown
10.0 out of 10, Exceptional, (42)
"The property was fantastic, clean, and wonderful! Would definitely stay again!"
United States
Alicia G.
The price is HK$2,438
HK$6,013 total
includes taxes & fees
5 Jan - 6 Jan 2026
NEW! Secluded retreat with private pool+chef's kitchen+hot tub+pond+theaterl!
Fridge, microwave, oven, stovetop
Country home with beautiful views and access to hiking, biking, and horse trails

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

Henryville
10.0 out of 10, Exceptional, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is HK$1,156
HK$1,931 total
includes taxes & fees
8 Dec - 9 Dec
Country home with beautiful views and access to hiking, biking, and horse trails
Exterior
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails

Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails

Lexington
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.
The price is HK$2,802
HK$6,077 total
includes taxes & fees
12 Dec - 13 Dec
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Madison
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is HK$1,253
HK$2,838 total
includes taxes & fees
9 Dec - 10 Dec
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Outdoor spa tub
1 Nordic Retreat in Brown County

1 Nordic Retreat in Brown County

Nashville
10.0 out of 10, Exceptional, (4)
"This place had everything (dog crate, Bluetooth speaker, leashes, plenty of towels). The just has created an incredible experience for visitors. We are planning to book again next year. "
United States
MrHaydenmusic
The price is HK$1,343
HK$3,721 total
includes taxes & fees
8 Dec - 9 Dec
1 Nordic Retreat in Brown County
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"Great little place. Location was exceptional. "
United States
Andrew P.
The price is HK$981
HK$1,307 total
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is HK$981
HK$1,898 total
includes taxes & fees
18 Dec - 19 Dec
The Artist’s A-Frame
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

Madison
10.0 out of 10, Exceptional, (36)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
The price is HK$1,549
HK$3,361 total
includes taxes & fees
8 Dec - 9 Dec
#207 King Suites, River Views, Deck, Downtown
Outdoor spa tub
1 Liberty Log Cabin in Brown County

1 Liberty Log Cabin in Brown County

Nashville
10.0 out of 10, Exceptional, (33)
"A nice and upscale stay. Quiet and private. "
United States
Steven
The price is HK$1,119
HK$3,180 total
includes taxes & fees
8 Dec - 9 Dec
1 Liberty Log Cabin in Brown County
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

Hanover
9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is HK$904
HK$1,962 total
includes taxes & fees
8 Dec - 9 Dec
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jennings County Hotel Reviews

Comfort Inn Edinburgh - Columbus

Comfort Inn Edinburgh - Columbus

10/10 Excellent
"Driving late Friday night from NC for a Zundsy Colts game, I left early because of a Winter Weather advisory that was to go into effect Saturday afternoon. I arrived much earlier than I had anticipated, at noon. It was very cold with a wind chill. When I got to the desk at noon, the lady was awesome, finding me a room so I wouldn't have to wait until the normal 3:00 check-in time. She was awesome. I have stayed here many times as a stopover for a Colts game. Five stars all day!"
John 1-night trip
Posted 3 days ago
Comfort Inn Edinburgh - Columbus