View of Jefferson County Courthouse in Madison. Indiana, United States.

Holiday Rentals in Jefferson County

  • 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 Jefferson County holiday rentals

Property grounds

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, (9 reviews)
"Welcoming host and cottage as described. Thanks! "
United States
Adam H.
The price is €166
includes taxes & fees
16 Jun - 17 Jun
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (12 reviews)
"Everything was wonderful."
United States
Nicole Lea
The price is €154
includes taxes & fees
15 Jun - 16 Jun
Maple Cozy Cabin at Lost Trails
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (12 reviews)
"We had a wonderful stay! Everything was clean, communication was great - it was the perfect weekend getaway!"
United Kingdom
Karen L.
The price is €168
includes taxes & fees
14 Jul - 15 Jul
Sassafras Woodland Cabin at Lost Trails
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is €154
includes taxes & fees
22 Jun - 23 Jun
Walnut Secluded Cabin at Lost Trails
Fridge, microwave, oven, stovetop

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (3 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.
Mulberry Secluded Cabin at Lost Trails
TV, fireplace

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is €201
includes taxes & fees
16 Jun - 17 Jun
Cabin on the Ridge: The Sequel
Exterior detail

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (27 reviews)
"Everything was great and we were taking care of excellently."
United States
Frank B.
Cedar Rustic Cabin at Lost Trails
Exterior detail

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, (18 reviews)
"Perfect place for our short stay! Had everything we needed and was super clean!! Would definitely stay there again!"
United Kingdom
Heather E.
The price is €119
includes taxes & fees
29 Jun - 30 Jun
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Nice cabin"
United States
Nathan M.
The price is €212
includes taxes & fees
16 Jun - 17 Jun
Cabin on the Ridge
Smart TV

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, (44 reviews)
"The property was clean and the host was very responsive prior to and during the stay ensuring a positive trip. "
United States
Natalie H.
The price is €214
includes taxes & fees
15 Jun - 16 Jun
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Outdoor dining

Charming 2-bedroom house with a river view in wonderful Madison

Charming 2-bedroom house with a river view in wonderful Madison
Madison
8.8 out of 10, Excellent, (3 reviews)
"The place was indeed charming. The host was wonderful and available for all questions! "
United States
Amy W.
Charming 2-bedroom house with a river view in wonderful Madison
Jetted bath, hair dryer, towels, soap

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
10.0 out of 10, Exceptional, (1 review)
"The host was extremely nice and allowed us to get into the loft a little early. The loft was really nice and we enjoyed out stay. "
United States
Judi K.
The price is €151
includes taxes & fees
1 Jul - 2 Jul
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Smart TV

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, (63 reviews)
"It was great! It had everything we needed!"
United States
Grace A.
The price is €213
includes taxes & fees
6 Jul - 7 Jul
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (33 reviews)
"Matt was a superb host. Probably the best rental experience I've had!"
United States
Shawnee T.
The price is €207
includes taxes & fees
25 Jun - 26 Jun
The Artist’s A-Frame
2 bedrooms, iron/ironing board, WiFi, bed sheets

Campus Cottage: Cozy, Convenient, Captivating on Hanover College Campus

Campus Cottage: Cozy, Convenient, Captivating on Hanover College Campus
Hanover
9.6 out of 10, Exceptional, (4 reviews)
"Everything was as described and clean. Beds were extremely comfortable and house was spotless. "
United States
Ed S.
The price is €202
includes taxes & fees
13 Jul - 14 Jul
Campus Cottage: Cozy, Convenient, Captivating on Hanover College Campus
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
Madison
10.0 out of 10, Exceptional, (37 reviews)
"Always a wonderful place to stay!"
United States
Leann L.
The price is €185
includes taxes & fees
17 Jun - 18 Jun
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Microwave, oven, stovetop, dishwasher

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, (16 reviews)
"Great property for a group outing. Great location."
United States
Paul S.
The price is €366
includes taxes & fees
12 Jul - 13 Jul
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Terrace/patio

"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
9.6 out of 10, Exceptional, (12 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is €329
includes taxes & fees
16 Jun - 17 Jun
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
Private kitchen

Unique! Edgar Allan Poe inspired Gothic themed home in Madison

Unique! Edgar Allan Poe inspired Gothic themed home in Madison
Madison
10.0 out of 10, Exceptional, (2 reviews)
"OMG, the place was incredible, we absolutely loved the place. We refer this place all my friends and family. Host was great, easy to work with and excellent instruction. Location was great too, a couple blocks off the main strip."
United States
Anonymous traveller
The price is €180
includes taxes & fees
15 Jun - 16 Jun
Unique! Edgar Allan Poe inspired Gothic themed home in Madison
Terrace/patio

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison
10.0 out of 10, Exceptional, (16 reviews)
"Great location and the host thought of everything to stock the house with."
United States
Kinni L.
The price is €340
includes taxes & fees
22 Jun - 23 Jun
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
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 Jefferson County Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"The room and hotel were clean. The staff was friendly. It was my first time in madison so I booked this hotel not really knowing much about it or the area but I will definitely book again!"
JayCee 6-night trip
Posted less than an hour ago
Hillside Inn

Find out more about Jefferson County

Holiday Homes in Jefferson County

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

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

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