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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
Property grounds

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

10.0 out of 10, Exceptional, (195)
"This cabin is the perfect place to getaway and relax! It’s peaceful and beautiful!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Charming 3-bedroom house in lovely downtown Madison.
Exterior

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
"Great old home and cool neighborhood. "
Charming 3-bedroom house in lovely downtown Madison.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

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

10.0 out of 10, Exceptional, (47)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Rustic cabin just outside of Madison!
4 bedrooms, free WiFi, bed sheets

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (42)
"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!
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (39)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is €217
includes taxes & fees
3 Sept - 4 Sept
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
9.8 out of 10, Exceptional, (9)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is €148
includes taxes & fees
3 Sept - 4 Sept
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Stoney Creek - Sit back and unwind
Interior

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (93)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind
Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

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

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is €122
includes taxes & fees
23 Sept - 24 Sept
Sunset over the city Suite 201, Sunset over the city Suite 201
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Outdoor spa tub

Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (18)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

10.0 out of 10, Exceptional, (8)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
The price is €301
includes taxes & fees
3 Sept - 4 Sept
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (19)
"I can't say enough about our stay at the Artist's A-Frame. The hosts are exceptional, the location is ideal, and the space is beautiful! I highly recommend and am anxious to return!"
The price is €208
includes taxes & fees
11 Sept - 12 Sept
The Artist’s A-Frame
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, (8)
"Clean, spacious, nicely decorated, comfortable bed. For us it was also nostalgic - from the windows on Main we could see the home where my husband’s mother was raised and the location of his grandparents’ grocery (in the latter 1930s- 1971).. now the Attic, a coffee, pastry, sandwich shop. "
The price is €200
includes taxes & fees
10 Sept - 11 Sept
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Fridge, microwave, oven, stovetop

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

9.6 out of 10, Exceptional, (17)
"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
3 Sept - 4 Sept
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Microwave, oven, stovetop, dishwasher

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The price is €409
includes taxes & fees
8 Sept - 9 Sept
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds

Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

9.6 out of 10, Exceptional, (5)
"This property was very quaint and clean. What a cute little town in Madison Indiana. "
The price is €111
includes taxes & fees
23 Sept - 24 Sept
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Rustic Cabin at Lost Trails
Exterior

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (12)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (8)
"My husband and I came to celebrate our anniversary and his retirement and to go hiking- our favorite activity together! This place was perfect! Location! Location! Location! Near everything- walked downtown to shops and restaurants! The place itself was clean, nicely decorated, and very welcoming We will e back! "
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Exterior

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
1 bedroom, WiFi, bed sheets

Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

9.4 out of 10, Exceptional, (8)
"We had a great time in Madison! The place was so small but it was a great little area! It's a great place to hang your hat for a few days!"
The price is €126
includes taxes & fees
23 Sept - 24 Sept
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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

Find out more about Jefferson County

Find out more about Jefferson County

Holiday Homes in Jefferson County

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