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Holiday Rentals in Jefferson County

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Featured Holiday Rentals in Jefferson County

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Enjoy serene lakeside views from the porch of this charming lakeside retreat, where you can relax and unwind amidst lush greenery.

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (189)
"Great getaway. View is fantastic!!! Location with plenty of privacy!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Enjoy cooking and socializing in this kitchen with a central island and bar stools, featuring stainless steel appliances and a pendant light fixture.

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

9.8 out of 10, Exceptional, (30)
"Clean, comfortable home with everything needed for our stay. "
The price is €219
includes taxes & fees
27 Jul - 28 Jul
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Modern kitchen with stainless steel appliances, light grey cabinetry, and a black and white patterned rug.

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (3)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Stoney Creek - Sit back and unwind
Enjoy cooking in this inviting kitchen with a central island, oven, and window overlooking the surrounding landscape.

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (87)
"My husband and our son stayed for two nights and had a great time! The cabin was clean and just overall really nice. The hot tub was fantastic! The owners were very communicative and responsive. Overall, this made for a perfect little getaway!"
Stoney Creek - Sit back and unwind
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Compact kitchen with modern design, featuring an oven, microwave, and window.

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (48)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Rustic cabin just outside of Madison!
Relax in a spacious room with a four-poster bed, wooden headboard, and a ceiling fan.

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (38)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!
Rustic Cabin at Lost Trails
Guests can enjoy a secluded retreat in this cabin, surrounded by mature trees and featuring a spacious porch with a railing.

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (5)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Relax in a comfortable living space with a sectional sofa and large mirror.

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (43)
"This is the second time staying at this unit. Next weekend, we are going down and staying in the upstairs loft. Looking forward. Always a great time staying with Suzie. Highly recommend."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
The Wadsworth in National Historic District of Madison, Indiana.
Enjoy cooking in this well-equipped kitchen with an oven and stovetop.

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (48)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fully equipped kitchen with microwave, stove, sink, and refrigerator.

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (4)
"Riverside Retreat is a must stay! It is a great location and exactly as described. Highly recommend. We will be back!"
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
Relax by the fire pit in a serene backyard setting with a seating area and pathway.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

10.0 out of 10, Exceptional, (44)
"We had a great stay and the communication was terrific. Thanks SW"
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Enjoy al fresco dining and socializing in this patio area, featuring a fire pit, bench, and table.

"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit

9.4 out of 10, Exceptional, (8)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Sunset over the city Suite 201, Sunset over the city Suite 201
Enjoy the view of the city from the comfort of your room, with a street scene unfolding outside.

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (8)
"It was wonderful "
The price is €126
includes taxes & fees
11 Aug - 12 Aug
Sunset over the city Suite 201, Sunset over the city Suite 201
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Enjoy al fresco dining on the patio with a grill and scenic views.

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (42)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry
Compact kitchen with a refrigerator, oven, and washing machine/dryer. Dining area with a table and chairs.

Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry

2.0 star property
9.4 out of 10, Exceptional, (9)
"Absolutely amazing stay!!! Beautiful house and comfort you cannot beat."
Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry
Clifty Falls Family Getaway-Sleeps 8--3 Miles to Historic Downtown & River Front
Relax in a spacious room with a large bed, ceiling fan, and window with blinds.

Clifty Falls Family Getaway-Sleeps 8--3 Miles to Historic Downtown & River Front

10.0 out of 10, Exceptional, (1)
"The location, cleanliness & appeal of this house are fantastic! The beds are very comfortable and the kitchen is well stocked. We would love to stay again. "
Clifty Falls Family Getaway-Sleeps 8--3 Miles to Historic Downtown & River Front
Historic city overlook suite 206, Historic city overlook suite 306
Relax in this serene bedroom with a large bed, a desk with a chair, and a potted plant.

Historic city overlook suite 206, Historic city overlook suite 306

9.8 out of 10, Exceptional, (6)
"This property has a great location and is perfect for a couple. Would have liked a tv and air unit in the bedroom but it all worked out just fine! We will be happy to stay again! "
The price is €142
includes taxes & fees
11 Aug - 12 Aug
Historic city overlook suite 206, Historic city overlook suite 306
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Welcome to our farmhouse, featuring a modern kitchen with a stainless steel refrigerator, microwave, and white cabinetry.

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

9.4 out of 10, Exceptional, (16)
"Perfect little cozy cabin for an amazing getaway! We were able to just relax and enjoy our time together with zero distractions. 10/10 would definitely stay here again! "
The price is €254
includes taxes & fees
15 Jul - 16 Jul
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Smart TV

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

10.0 out of 10, Exceptional, (4)
"Bed was comfortable. We loved the decor. I look forward to coming back."
The price is €201
includes taxes & fees
20 Jul - 21 Jul
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Hardy lake house. Ideal for relax fishing and spending quality time on lake.
Sit by the fire pit surrounded by natural seating and lush greenery.

Hardy lake house. Ideal for relax fishing and spending quality time on lake.

2.0 star property
9.8 out of 10, Exceptional, (18)
"Home was exactly as described, very well kept and host was great! "
Hardy lake house. Ideal for relax fishing and spending quality time on lake.
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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