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

Jennings County Vacation Rentals

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Our top choices for Jennings County vacation rentals

Property grounds

1. COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW

COZY LAKEHOUSE PRIVATE SETTING - LAKE FRONT VIEW
North Vernon
9.8 out of 10, Exceptional, (18 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 CA $452
CA $586 total
includes taxes & fees
Sep 4 - Sep 5
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, (129 reviews)
"What a great place to stay for a weekend getaway. Looking forward to staying there again."
United States
Alison
The price is CA $129
CA $212 total
includes taxes & fees
Sep 2 - Sep 3
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy
Exterior

3. Buggy Shed

Buggy Shed
Versailles
10.0 out of 10, Exceptional, (1 review)
"Clean, pet friendly, and near the 2 state parks we wanted to see. Easy to check in and host was quick to communicate with us! We stayed at the school house and it was nice!"
United States
Ron L.
The price is CA $215
CA $273 total
includes taxes & fees
Sep 3 - Sep 4
Buggy Shed
Interior

4. 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 CA $215
CA $272 total
includes taxes & fees
Aug 31 - Sep 1
School Days
Exterior

5. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (39 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 CA $168
CA $326 total
includes taxes & fees
Aug 30 - Aug 31
The Artist’s A-Frame
Smart TV

6. 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, (49 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 CA $161
CA $343 total
includes taxes & fees
Sep 8 - Sep 9
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior

7. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 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 CA $139
CA $240 total
includes taxes & fees
Sep 3 - Sep 4
Maple Cozy Cabin at Lost Trails
Exterior

8. Beautiful, cozy, lakeside wooded getaway in serene surroundings.

Beautiful, cozy, lakeside wooded getaway in serene surroundings.
Osgood
10.0 out of 10, Exceptional, (7 reviews)
"The property is located in such a lovely peaceful setting. Early morning on the patio listening to the birds is calming. The inside of the property is charming and everything is spotless. Very nice and we will return if we ever go back through the area again."
United States
Vicki M.
The price is CA $242
CA $306 total
includes taxes & fees
Aug 30 - Aug 31
Beautiful, cozy, lakeside wooded getaway in serene surroundings.
Dining

9. Unwind Haven

Unwind Haven
Versailles
8.0 out of 10, Very good, (1 review)
The price is CA $215
CA $272 total
includes taxes & fees
Aug 31 - Sep 1
Unwind Haven
Property grounds

10. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (7 reviews)
"A lovely accommodation! The cabin was spotless, well kept and comfortable, and the property was private and quiet. Great hosts that were very responsive and quick to help with anything. Would absolutely recommend!"
United States
Shirley Z.
The price is CA $172
CA $240 total
includes taxes & fees
Sep 14 - Sep 15
Briar Ridge Cabin in Osgood IN
Terrace/patio

11. 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 CA $139
CA $240 total
includes taxes & fees
Aug 31 - Sep 1
Walnut Secluded Cabin at Lost Trails
Exterior

12. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is CA $124
CA $223 total
includes taxes & fees
Sep 7 - Sep 8
Sassafras Woodland Cabin at Lost Trails
Terrace/patio

13. Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16

Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Great house. Quiet location. Easy walk to main street resturanrs and shops."
United States
christine g.
The price is CA $423
CA $1,012 total
includes taxes & fees
Aug 31 - Sep 1
Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
TV, fireplace, DVD player

14. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is CA $168
CA $326 total
includes taxes & fees
Aug 30 - Aug 31
Cabin on the Ridge
Coffee/tea maker, fridge, microwave, oven

15. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
The price is CA $139
CA $240 total
includes taxes & fees
Aug 30 - Aug 31
Mulberry Secluded Cabin at Lost Trails
Property grounds

16. 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)
"Very close to downtown restaurants and shopping. The trails out back were nice and relaxing to walk on. The property was quiet and relaxing. Perfect size for my wife and I and our 12 pound dog. The dog loved the trails and kept us busy on his walks."
United States
Dean
The price is CA $148
CA $266 total
includes taxes & fees
Sep 1 - Sep 2
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Outdoor spa tub

17. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Such a cute little place for my husband and I to get away for my birthday weekend! The house was adorable, well stocked for daily needs and very clean! Will definitely stay here again and recommend it to others!! "
United States
Claire S.
The price is CA $263
CA $451 total
includes taxes & fees
Sep 20 - Sep 21
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Outdoor dining

18. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful view of the river! Nice location and easy to find. Highly recommend for a group getaway. "
United States
Beverly L.
The price is CA $330
CA $597 total
includes taxes & fees
Sep 2 - Sep 3
T&E Riverhouse Retreat
Terrace/patio

19. Spacious family cabin with game room and backyard!

Spacious family cabin with game room and backyard!
Hanover
9.4 out of 10, Exceptional, (3 reviews)
"This was the perfect place for our girl's weekend! The place was super clean, cozy, and made for fun. The host was incredibly responsive and quickly jumped on the phone with me to help solve a check-in issue I had. Great and easy location to get to!"
United States
Brianna S.
The price is CA $255
CA $771 total
includes taxes & fees
Aug 31 - Sep 1
Spacious family cabin with game room and backyard!
Microwave, oven, stovetop, dishwasher

20. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison
9.8 out of 10, Exceptional, (24 reviews)
"Great stay and beautiful house. The location was really outstanding and many restaurants, boutiques, and coffee shops were within walking distance. "
United States
Stephanie B.
The price is CA $186
CA $662 total
includes taxes & fees
Aug 30 - Aug 31
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
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
"Clean; great view; friendly staff; close to downtown"
Stacy 1-night trip
Posted 2 days ago
Hillside Inn

Find out more about Jennings County

Everything you need to know about Jennings County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jennings County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jennings County vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jennings County vacation rentals we have selected for you start as low as CA $212 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 vacation 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 vacation.

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.