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

Vacation Homes in Jennings County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Jennings County vacation homes

An outdoor patio with a table and chairs, a canopy, and string lights.

1. Red comfy cottage

Red comfy cottage
Madison
9.8 out of 10, Exceptional, (90 reviews)
"Everything was very nice and our host was very helpful with any of our needs."
United States
Amy C.
Red comfy cottage
A wooden cabin with a porch, a staircase, and a deck.

2. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (17 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AED 338
AED 602 total
includes taxes & fees
9 Nov - 10 Nov
Sassafras Woodland Cabin at Lost Trails
Enjoy the stars from the private hot tub while enjoying the firepit

3. 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, (20 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.
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
A cabin with a wooden deck, a staircase, and a porch.

4. Riverside Cabin w/ 3 Decks in North Vernon!

Riverside Cabin w/ 3 Decks in North Vernon!
North Vernon
10.0 out of 10, Exceptional, (39 reviews)
"Lovely private property! Such a relaxing stay! The place was incredibly clean with attention to special details to make our stay extra lovely! Quick and easy communication from our host."
United States
Craig P.
Riverside Cabin w/ 3 Decks in North Vernon!
A modern kitchen with a central island, dining area with chairs, and a cozy living room with a sofa and ottoman.

5. Charming 2-bedroom house in Devil's Elbow Osgood, IN

Charming 2-bedroom house in Devil's Elbow Osgood, IN
Osgood
9.8 out of 10, Exceptional, (16 reviews)
"This is a great place to stay for a family of 4. The open living area/kitchen is perfect for down time and the back patio is nice for an evening outdoors. The best was the location right by the family we were visiting. Definitely will choose this place again!"
United States
Kristen T.
Charming 2-bedroom house in Devil's Elbow Osgood, IN
A two-story wooden cabin with a balcony, situated by a lake with a stone wall foundation.

6. Pine Lodge at Lost Trails

Pine Lodge at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (4 reviews)
"Brilliant stay. Wish we had longer!"
United States
Catherine T.
Pine Lodge at Lost Trails
A kitchen with wooden cabinets, a stove, and a wooden staircase.

7. Madison's Only YURT Experience

Madison's Only YURT Experience
Madison
9.2 out of 10, Wonderful, (11 reviews)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
United States
Nicole E.
Madison's Only YURT Experience
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

8. 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, (78 reviews)
"Love the stay very relaxed"
United States
Steve C.
The price is AED 380
AED 805 total
includes taxes & fees
14 Oct - 15 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A white house with a wooden door, a covered porch, and a well-maintained garden.

9. Bungalow on Main!!

Bungalow on Main!!
Madison Historic District
9.8 out of 10, Exceptional, (39 reviews)
Bungalow on Main!!
A kitchen with wooden cabinets, granite countertop, built-in oven, and a refrigerator.

10. Hilltop Haven

Hilltop Haven
Madison
9.6 out of 10, Exceptional, (5 reviews)
"Nice house and kid friendly. Very close to town. We will be back to Madison loved the town. House was too big for the two of us but if I come with a bigger group I would stay here again."
United States
Christina N.
Hilltop Haven
A hallway with a carpeted floor, wooden doors with glass panels, a television mounted on the wall, and a window with blinds.

11. Cozy Downtown 3 Bedroom

Cozy Downtown 3 Bedroom
Columbus
9.2 out of 10, Wonderful, (19 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 AED 294
AED 749 total
includes taxes & fees
15 Oct - 16 Oct
Cozy Downtown 3 Bedroom
A kitchen with a brick wall, wooden cabinets, a central island with bar stools, and pendant lighting.

12. 2nd Street Inn: Historic 1870s Gem Steps From Main

2nd Street Inn: Historic 1870s Gem Steps From Main
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"This place is absolutely adorable. We stayed here to celebrate my daughter's birthday with a couple friends. The location was perfect for exploring Madison, just steps away from the water and the main road. The house looked to be recently renovated and was so cute. The beds were very comfortable and there was more space than what appeared in the photos. We would absolutely stay here again. The only minor issues we had was the AC took many hours to cool from the 76 degrees it was set to when we...
United States
Christi S.
2nd Street Inn: Historic 1870s Gem Steps From Main
A tranquil pond with a wooden dock and a gazebo, surrounded by lush greenery and a house in the background.

13. Secluded Country Home in Historic Hoosier Hills

Secluded Country Home in Historic Hoosier Hills
Vevay
10.0 out of 10, Exceptional, (133 reviews)
"Great host , property was exactly as advertised, would definitely recommend this property "
United States
Mark S.
Secluded Country Home in Historic Hoosier Hills
A modern kitchen with white cabinets, a granite countertop, and a central island with bar stools.

14. The Wadsworth in National Historic District of Madison, Indiana.

The Wadsworth in National Historic District of Madison, Indiana.
Madison Historic District
10.0 out of 10, Exceptional, (81 reviews)
"Perfect location for a relaxed few days with a dear friend! Loved it!"
United States
Patti B.
The Wadsworth in National Historic District of Madison, Indiana.
A modern kitchen with granite countertops, stainless steel appliances, and dark wood cabinets.

15. East End River Retreat: Dogs Welcome!

East End River Retreat: Dogs Welcome!
Madison Historic District
10.0 out of 10, Exceptional, (36 reviews)
"We had a delightful stay at East End River Retreat. Clean, well furnished, an overall wonderful experience in spite of the town being without electricity!"
United States
Melissa Y.
East End River Retreat: Dogs Welcome!
An outdoor patio with a hot tub, a fire pit, and string lights.

16. "Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
Madison Historic District
9.8 out of 10, Exceptional, (17 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is AED 537
AED 1,433 total
includes taxes & fees
14 Oct - 15 Oct
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

17. 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, (53 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 AED 479
AED 991 total
includes taxes & fees
22 Oct - 23 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
An aerial view of a water park with multiple swimming pools, slides, and a large blue spiral water feature.

18. #209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison Historic District
10.0 out of 10, Exceptional, (72 reviews)
"The house was clean, comfortable, and had everything we needed. The location was great; very close to restaurants and shops on Main Street as well as the parks by the river. "
United States
Hannah M.
The price is AED 828
AED 1,842 total
includes taxes & fees
19 Oct - 20 Oct
#209 Kings, River View, Deck, Bicentennial Park
A wooden door with a sliding mechanism, a wooden wall, and a wooden bench with baskets.

19. Pet-Friendly Home w/ River Access in Crothersville

Pet-Friendly Home w/ River Access in Crothersville
Crothersville
9.4 out of 10, Exceptional, (3 reviews)
"We had a fantastic time. We had absolutely everything we needed. What a beautiful farm it was."
United States
Kay H.
Pet-Friendly Home w/ River Access in Crothersville
A fireplace with a stone facade, a mounted flat-screen TV above it, and a marble mantel.

20. Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Madison Historic District
9.6 out of 10, Exceptional, (36 reviews)
"Great location very clean"
United States
Karen G.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
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

Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"This cabin did a great job providing what you would need for an overnight stay in this area."
Olivia 1-night trip
Posted 1 hour ago
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

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