Photo by Susan Ross

Holiday Rentals in Jennings County

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

Our top choices for Jennings County holiday rentals

Fridge, microwave, oven, stovetop
Charming Historic Retreat Home

Charming Historic Retreat Home

Charming Historic Retreat Home
Vernon
10.0 out of 10, Exceptional, (18)
"Great place with lots of charm. "
United States
Jennifer W.
Charming Historic Retreat Home
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!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (53)
"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 €195
includes taxes & fees
28 Dec - 29 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (4)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
Cozy Tiny House in Scottsburg
Property grounds
Downtown Columbus~Stunning Upscale 1 bd Suite

Downtown Columbus~Stunning Upscale 1 bd Suite

Downtown Columbus~Stunning Upscale 1 bd Suite
Columbus
9.8 out of 10, Exceptional, (6)
"A beautiful property and a great location. Highly recommended!"
United States
bryony
Downtown Columbus~Stunning Upscale 1 bd Suite
Exterior
Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (17)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is €193
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin on the Ridge: The Sequel
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is €199
includes taxes & fees
4 Jan - 5 Jan 2026
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
TV, fireplace, DVD player
Cabin on the Ridge Su

Cabin on the Ridge Su

Cabin on the Ridge Su
Madison
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
Cabin on the Ridge Su
1 bedroom, WiFi, bed sheets
East Main Lofts - Boho 203

East Main Lofts - Boho 203

East Main Lofts - Boho 203
Madison
9.6 out of 10, Exceptional, (8)
"Very tasteful loft in convenient location. Enjoyed our stay."
United States
Teresa P.
The price is €303
includes taxes & fees
28 Dec - 29 Dec
East Main Lofts - Boho 203
Interior
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison
9.6 out of 10, Exceptional, (14)
"Perfect little space for our weekend getaway. Great location, everything was very clean and up to date. "
United States
brad h.
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Exterior
The Artist’s A-Frame

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 Artist’s A-Frame
Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy
2.0 star property
Columbus
9.6 out of 10, Exceptional, (58)
"It was amazing stay!"
United States
Anas
The price is €126
includes taxes & fees
4 Jan - 5 Jan 2026
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

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
2.0 star property
Vallonia
10.0 out of 10, Exceptional, (14)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is €258
includes taxes & fees
30 Dec - 31 Dec
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (37)
"Wonderful place. Been here a few times. Just perfect with a great balcony and view. "
United States
Patrick L.
#207 King Suites, River Views, Deck, Downtown
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!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.8 out of 10, Exceptional, (34)
"Great place to stay for Hanover college "
United States
Lindsey M.
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Fridge, microwave, oven, stovetop
Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi

Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi

Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi
Columbus
9.8 out of 10, Exceptional, (6)
"I stayed here with my husband and my mother, and we all loved it! The apartment was very modern and clean, and was in a great location. I would definitely recommend staying here, and hope to do so again in the near future!"
United States
Vivian K.
Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi
Fridge, microwave, oven, stovetop
#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison
10.0 out of 10, Exceptional, (62)
"Great house, great location and the host was very responsive! I would definitely recommend this place. "
United States
Lisa C.
#209 Kings, River View, Deck, Bicentennial Park
Property grounds
Walkable Downtown Getaway (FREE Bikes to use)

Walkable Downtown Getaway (FREE Bikes to use)

Walkable Downtown Getaway (FREE Bikes to use)
Columbus
10.0 out of 10, Exceptional, (3)
"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.
Walkable Downtown Getaway (FREE Bikes to use)
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 Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Madison
10.0 out of 10, Exceptional, (14)
"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.
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
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

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
10.0 out of 10, Exceptional, (30)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is €221
includes taxes & fees
29 Dec - 30 Dec
Country home with beautiful views and access to hiking, biking, and horse trails
Fridge, microwave, oven, stovetop
Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest
Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
Modern Nature Cabin | Private Escape in the Forest
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

Fairfield Inn & Suites by Marriott Columbus, IN

Fairfield Inn & Suites by Marriott Columbus, IN

10/10 Excellent
"clean, friendly staff, "
Lester 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Columbus, IN

Find out more about Jennings County

Holiday Homes in Jennings County

Search for holiday homes in Jennings County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Jennings County using one of the methods below: 

  • View our selection of featured holiday homes in Jennings County
  • Use the map to find apartments and other holiday rentals in the Jennings County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Jennings County while they last

Look no further and take a look at our great range of rental properties in Jennings County!