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

Jennings County Holiday Rentals

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Top Cities in Jennings County

A waterfall in a forested area with a muddy pool at its base.
Holiday RentalsHoliday Rentals

North Vernon

North Vernon

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 NZ$601
includes taxes & fees
3 Nov - 4 Nov
COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW
View from property

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, (152 reviews)
"Very similar to other campgrounds but it did have some privacy."
United States
Brandon
The price is NZ$272
includes taxes & fees
30 Nov - 1 Dec
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy
A wooden cabin with a porch, a staircase, and a deck.

3. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is NZ$303
includes taxes & fees
3 Nov - 4 Nov
Sassafras Woodland Cabin at Lost Trails
2

4. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 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 NZ$303
includes taxes & fees
29 Nov - 30 Nov
Maple Cozy Cabin at Lost Trails
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

5. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 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 NZ$397
includes taxes & fees
2 Nov - 3 Nov
Modern cabin very close to scenic riverfront walks
A wooden deck with a 'WELCOME' sign, surrounded by trees and a path.

6. 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 NZ$294
includes taxes & fees
2 Nov - 3 Nov
Briar Ridge Cabin in Osgood IN
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

7. 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 NZ$303
includes taxes & fees
18 Nov - 19 Nov
Walnut Secluded Cabin at Lost Trails
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a coffee maker, and a refrigerator.

8. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
9.8 out of 10, Exceptional, (6 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 NZ$328
includes taxes & fees
2 Nov - 3 Nov
Charming new tiny house-Friendship IN
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

9. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"We loved the cabin, it had everything we needed - lovely peaceful surroundings, and was very clean! Thank you."
United States
Lisa S.
The price is NZ$303
includes taxes & fees
18 Nov - 19 Nov
Mulberry Secluded Cabin at Lost Trails
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

10. 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
9.2 out of 10, Wonderful, (15 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is NZ$195
includes taxes & fees
16 Nov - 17 Nov
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A wooden deck with wicker furniture and a ceiling fan.

11. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (32 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is NZ$299
includes taxes & fees
1 Dec - 2 Dec
Cedar Rustic Cabin at Lost Trails
A kitchen with white cabinets, a stainless steel refrigerator, a black countertop, and a window with a black valance.

12. Downtown Columbus

Downtown Columbus
Columbus
9.8 out of 10, Exceptional, (32 reviews)
"This place was just perfect for us! Cute little neighborhood! Clean and comfortable, we will be back soon!!"
United States
Meghan I.
Downtown Columbus
Property grounds

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (19 reviews)
"Clean and cozy"
United States
Julie
The price is NZ$288
includes taxes & fees
4 Nov - 5 Nov
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A modern bedroom with a fireplace, a bed, a TV, and artwork on the walls.

14. Walkable Downtown Getaway (FREE Bikes to use)

Walkable Downtown Getaway (FREE Bikes to use)
Columbus
9.8 out of 10, Exceptional, (6 reviews)
"Clean and simple place to stay with great access to downtown Columbus - perfect for enjoying restaurants and architecture tours offered by the town."
United States
Lincoln G.
The price is NZ$278
includes taxes & fees
5 Nov - 6 Nov
Walkable Downtown Getaway (FREE Bikes to use)
A large bronze sculpture in a public square with a historic building in the background.

15. Downtown Getaway ~ Historic & Peaceful, FREE Bikes

Downtown Getaway ~ Historic & Peaceful, FREE Bikes
Columbus
9.8 out of 10, Exceptional, (9 reviews)
"Enjoyed our quick visit! Would rent again. Thanks"
United States
Ashley G.
The price is NZ$283
includes taxes & fees
2 Nov - 3 Nov
Downtown Getaway ~ Historic & Peaceful, FREE Bikes
A room with a bed, two armchairs, a small table, and a microwave.

16. Tiny Lakeside Cottage I 50 Acres of Gardens

Tiny Lakeside Cottage I 50 Acres of Gardens
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is NZ$534
includes taxes & fees
2 Nov - 3 Nov
Tiny Lakeside Cottage I 50 Acres of Gardens
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

17. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (23 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is NZ$467
includes taxes & fees
1 Dec - 2 Dec
Cabin on the Ridge
A hallway with a carpeted floor, wooden doors with glass panels, a television mounted on the wall, and a window with blinds.

18. Cozy Downtown 3 Bedroom

Cozy Downtown 3 Bedroom
Columbus
9.2 out of 10, Wonderful, (20 reviews)
"Extremely attentive and responsive hosts. Great space in walking distance from every thing downtown. Would definitely book again."
United States
Sarah S.
The price is NZ$350
includes taxes & fees
2 Nov - 3 Nov
Cozy Downtown 3 Bedroom
A rustic interior with a wooden staircase, stone walls, and a dining area with chairs and a table.

19. School Days

School Days
Versailles
10.0 out of 10, Exceptional, (1 review)
"The Schoolhouse was a unique experience that we enjoyed very much! We were provided with anything that we would have needed for a comfortable stay. Our host communicated promptly whenever we needed. We appreciated the cleaniless of the home. We did not realize how close in proximity we would be with the other rentals on the property, but once inside, we felt like we had privacy. This would be a great stay for a couple or small family."
United States
Lora S.
The price is NZ$380
includes taxes & fees
2 Nov - 3 Nov
School Days
A cozy room with a bed, a chair, a sofa, and a small table.

20. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is NZ$297
includes taxes & fees
9 Nov - 10 Nov
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of 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.
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Top Jennings County Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"The location is ideal to view Madison from up high. A nice hotel with a good breakfast."
Don 1-night trip
Posted 2 hours ago
Hillside Inn

Find out more about Jennings County

Everything you need to know about Jennings County 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 Jennings County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Jennings County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jennings County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jennings County. 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 Jennings County 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 Jennings County holiday rentals we have selected for you start as low as NZ$272 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jennings County rentals

At Expedia, we put the best Jennings County 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 Jennings County 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 Jennings County 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 Jennings County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.