A gravel road flanked by tall grasses and a large tree.

Jennings County Holiday Rentals

  • 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

Our top choices for Jennings County holiday rentals

A tree with a tire swing hanging from it, a wooden deck with a railing, and a body of water in the background.

1. COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW
North Vernon
9.8 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay tremendously. The host is extremely kind and attentive. The accommodations and everything the property has to offer is remarkable. We will definitely be staying here again! "
United States
stepan a.
The price is HK$2,157
HK$2,636 total
includes taxes & fees
6 Oct - 7 Oct
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

2. Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy
2.5 star property
Columbus
9.6 out of 10, Exceptional, (134 reviews)
"What a great place to stay for a weekend getaway. Looking forward to staying there again."
United States
Alison
The price is HK$793
HK$1,273 total
includes taxes & fees
1 Oct - 2 Oct
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

3. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (128 reviews)
"Very well kept and beautiful home to stay in. The hot tub, for pit, and wrap around porch were all very nice amenities."
United States
Daniel N.
The price is HK$981
HK$1,985 total
includes taxes & fees
5 Oct - 6 Oct
Stoney Creek - Sit back and unwind

4. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (14 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is HK$784
HK$1,357 total
includes taxes & fees
28 Sept - 29 Sept
Maple Cozy Cabin at Lost Trails
A wooden cabin with a porch, a staircase, and a deck.

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is HK$714
HK$1,276 total
includes taxes & fees
26 Oct - 27 Oct
Sassafras Woodland Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

6. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is HK$784
HK$1,357 total
includes taxes & fees
28 Sept - 29 Sept
Mulberry Secluded Cabin at Lost Trails

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is HK$699
HK$1,345 total
includes taxes & fees
29 Sept - 30 Sept
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A wooden deck with a 'WELCOME' sign, surrounded by trees and a path.

8. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (9 reviews)
"5 star stay forgot my fishing 🎣 😒 pole , just like being back in holler in nc"
United States
Kelsie
The price is HK$988
HK$1,371 total
includes taxes & fees
30 Sept - 1 Oct
Briar Ridge Cabin in Osgood IN
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

9. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is HK$784
HK$1,357 total
includes taxes & fees
19 Oct - 20 Oct
Walnut Secluded Cabin at Lost Trails
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

10. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is HK$863
HK$1,447 total
includes taxes & fees
6 Oct - 7 Oct
Cedar Rustic Cabin at Lost Trails
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

11. 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
9.6 out of 10, Exceptional, (52 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
The price is HK$1,012
HK$2,021 total
includes taxes & fees
26 Oct - 27 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A modern living room with a sofa, a green armchair, a coffee table, and a bookshelf filled with plants and decorative items.

12. Walkable Historic Home (FREE Bikes to use)

Walkable Historic Home (FREE Bikes to use)
Columbus
9.4 out of 10, Exceptional, (12 reviews)
"Nice place and clean"
United States
Kathy J.
The price is HK$824
HK$1,276 total
includes taxes & fees
28 Sept - 29 Sept
Walkable Historic Home (FREE Bikes to use)
A covered porch with a wooden door, potted plants, and a metal railing.

13. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (40 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is HK$988
HK$1,863 total
includes taxes & fees
29 Sept - 30 Sept
The Artist’s A-Frame
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a coffee maker, and a refrigerator.

14. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (4 reviews)
"This tiny home was exactly what we had expected. Very clean, nice and welcoming. The owners were great and communication was excellent. We will be sure to see if it is Ava when we come to visit family again. "
United States
Randall B.
The price is HK$690
HK$1,520 total
includes taxes & fees
28 Sept - 29 Sept
Charming new tiny house-Friendship IN
A brick pathway lined with trees and a black iron fence, leading to a building with a brick facade.

15. Walkable Cozy Downtown Studio (FREE Bikes to use)

Walkable Cozy Downtown Studio (FREE Bikes to use)
Columbus
7.4 out of 10, Good, (3 reviews)
"The location was excellent and the place was clean. Easy to check in and out. "
United States
Mary C.
The price is HK$694
HK$1,156 total
includes taxes & fees
28 Sept - 29 Sept
Walkable Cozy Downtown Studio (FREE Bikes to use)
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

16. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is HK$566
HK$1,021 total
includes taxes & fees
28 Sept - 29 Sept
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A covered patio with a door, two wicker chairs, and string lights.

17. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is HK$824
HK$1,581 total
includes taxes & fees
24 Oct - 25 Oct
Cozy Tiny House in Scottsburg
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

18. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.6 out of 10, Exceptional, (19 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is HK$573
HK$1,640 total
includes taxes & fees
13 Oct - 14 Oct
Modern cabin very close to scenic riverfront walks
A cozy wooden cabin interior with a sofa, a dining table, and a TV.

19. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is HK$1,114
HK$1,923 total
includes taxes & fees
1 Oct - 2 Oct
Cabin on the Ridge: The Sequel
A brick pathway lined with trees and a black iron fence.

20. Downtown Getaway ~ Historic & Peaceful, FREE Bikes

Downtown Getaway ~ Historic & Peaceful, FREE Bikes
Columbus
9.8 out of 10, Exceptional, (8 reviews)
"Enjoyed our quick visit! Would rent again. Thanks"
United States
Ashley G.
The price is HK$852
HK$1,321 total
includes taxes & fees
28 Sept - 29 Sept
Downtown Getaway ~ Historic & Peaceful, FREE Bikes
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 Madison near Clifty Falls

Comfort Inn Madison near Clifty Falls

10/10 Excellent
"Perfect lotion"
Bobbie 2-night trip
Posted 2 hours ago
Comfort Inn Madison near Clifty Falls