A town with a prominent red brick building featuring a gold dome and clock tower, a bridge over a river, and lush green trees.

Vacation Homes in Jefferson County

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Jefferson County vacation homes

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

1. Red comfy cottage

Red comfy cottage
Madison
10.0 out of 10, Exceptional, (91 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
9.8 out of 10, Exceptional, (18 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AED 320
AED 603 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, (5 reviews)
"We were so happy with our stay at this property! The house was so clean, spacious, and felt brand-new. With 3 different living levels, it gave our family plenty of room! And the large, wrap-around porch gave such a nice place to relax outside. Furnishings were very nice, as was the decor and attention to detail. They literally thought of everything in this rental! The house was well-stocked with everything we needed. And communication with the host was super easy. We visited this...
United States
Amber S.
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)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is AED 380
AED 809 total
includes taxes & fees
26 Oct - 27 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

9. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (27 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A white house with a wooden door, a covered porch, and a well-maintained garden.

10. Bungalow on Main!!

Bungalow on Main!!
Madison Historic District
9.8 out of 10, Exceptional, (40 reviews)
"Great place to stay!! Close to everything, very clean and quiet. Hot tub was fantastic. Will definitely stay again!"
United States
Erin D.
Bungalow on Main!!
A kitchen with wooden cabinets, granite countertop, built-in oven, and a refrigerator.

11. Hilltop Haven

Hilltop Haven
Madison
9.8 out of 10, Exceptional, (6 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 porch with three white rocking chairs, a blue door with a wreath, and a brick pathway leading to the door.

12. Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays

Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays
Crestwood
9.6 out of 10, Exceptional, (15 reviews)
"We had a great stay. Host was responsive and friendly. The house was adorable and well kept. Everything worked great and had a great stocked coffee bar! Would recommend."
United States
Shawna C.
Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays
A kitchen with a brick wall, wooden cabinets, a central island with bar stools, and pendant lighting.

13. 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, (2 reviews)
"Awesome place!! Very good location!"
United States
Cherydan H.
2nd Street Inn: Historic 1870s Gem Steps From Main
A hot tub with a view of a lake at dusk, surrounded by trees and outdoor seating.

14. Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8
Prospect
9.6 out of 10, Exceptional, (109 reviews)
"The property was very cozy and inviting. It had plenty of room to accommodate my large group, and the beds were very comfortable. It's close to other amenities but secluded enough to feel private. We had a great stay and would gladly do stay here again."
United States
Kari M.
Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8
A tranquil pond with a wooden dock and a gazebo, surrounded by lush greenery and a house in the background.

15. 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 spacious living room with a large window overlooking a lake, a ceiling fan, and a wooden coffee table.

16. Waterfront Cabin | Near ARK | Large Family Retreat

Waterfront Cabin | Near ARK | Large Family Retreat
Warsaw
8.4 out of 10, Very good, (14 reviews)
"The beds weren't the most comfortable and the basement bathroom was a little noisy. But the space and the view were amazing. There are stores, restaurants, and a park in walkng distance. The kitchen and bathroom were pretty well stocked for cooking and toiletries. The hosts were very nice. We had a great time and would book again if we are ever back in Warsaw."
United States
Anonymous traveler
The price is AED 679
AED 1,915 total
includes taxes & fees
25 Oct - 26 Oct
Waterfront Cabin | Near ARK | Large Family Retreat
A modern kitchen with white cabinets, a granite countertop, and a central island with bar stools.

17. 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, (82 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.

18. 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.

19. "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)
"Loved our stay at Madison Manor. It was beautiful and nicely situated. It fit our needs and would highly recommend it."
United States
Norris F.
The price is AED 537
AED 1,420 total
includes taxes & fees
26 Oct - 27 Oct
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
A deck with wicker chairs, a table with a fire pit, and a view of a lake.

20. The Riverside Retreat - Your Coastal Getaway

The Riverside Retreat - Your Coastal Getaway
Prospect
9.6 out of 10, Exceptional, (57 reviews)
"Nice place right on the river! Easy and prompt communication."
United States
Dana H.
The Riverside Retreat - Your Coastal Getaway
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 Jefferson County Hotel Reviews

Super 8 by Wyndham Madison IN

Super 8 by Wyndham Madison IN

10/10 Excellent
"Will be staying here a lot when we take a weekend getaway 🍿🍿"
Rhea 2-night trip
Posted 6 hours ago
Super 8 by Wyndham Madison IN

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