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Jefferson County Holiday Rentals

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Featured Jefferson County Holiday Rentals

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, (41)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is HK$817
HK$1,736 total
includes taxes & fees
22 Oct - 23 Oct
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
10.0 out of 10, Exceptional, (12)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is HK$981
HK$1,307 total
includes taxes & fees
9 Oct - 10 Oct
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
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, (52)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
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, (47)
"It was a very nice and clean property, and it was a very relaxing vacation. Crossing the creek very amazing. And our host offered a very comforting place and enjoyed the seeing this part of Indiana. "
Rustic cabin just outside of Madison!
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (20)
"Great location to walk around town or to the river. House is charming with nice updates and bigger than it looks from the outside. Great stay. "
Bungalow on Main!!
Charming 3-bedroom house in lovely downtown Madison.
Exterior

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
8.8 out of 10, Excellent, (6)
Charming 3-bedroom house in lovely downtown Madison.
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, (205)
"Very nice log cabin in a very secluded location with a small pond.We enjoyed it very much."
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
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, (18)
"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 HK$1,401
HK$2,256 total
includes taxes & fees
11 Oct - 12 Oct
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
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, (10)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is HK$732
HK$1,195 total
includes taxes & fees
15 Oct - 16 Oct
Sunset over the city Suite 201, Sunset over the city Suite 201
"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, (11)
"We thoroughly enjoyed our time there, and the little extra touches were a pleasant surprise! The house was incredibly clean and the owner was very prompt and responsive to questions we had. Definitely would stay again!"
The price is HK$1,183
HK$2,766 total
includes taxes & fees
29 Oct - 30 Oct
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Stoney Creek - Sit back and unwind
Interior

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (95)
"Stayed with my Wife for a week after our wedding and it the perfect place to recharge after the rollercoaster of emotions that we had dealt with during the wedding. Would definitely recommend to anyone who is looking for a relaxing and comfortable place to stay. "
Stoney Creek - Sit back and unwind
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, (14)
"Great one bedroom apartment! It was clean and great location for our quick getaway."
The price is HK$834
HK$1,648 total
includes taxes & fees
12 Oct - 13 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Alterra:Slees 8,Steps to Main St,Serene
3 bedrooms, iron/ironing board, WiFi, bed sheets

Alterra:Slees 8,Steps to Main St,Serene

10.0 out of 10, Exceptional, (1)
"Home is beautiful. Great stay."
Alterra:Slees 8,Steps to Main St,Serene
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop

Modern Nature Cabin | Private Escape in the Forest

9.8 out of 10, Exceptional, (6)
The price is HK$691
HK$1,702 total
includes taxes & fees
16 Oct - 17 Oct
Modern Nature Cabin | Private Escape in the Forest
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Fridge, microwave, oven, stovetop

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (57)
"Home was the perfect setting for our yearly girl’s get together!"
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (22)
"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 HK$981
HK$1,906 total
includes taxes & fees
20 Oct - 21 Oct
The Artist’s A-Frame
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds

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

9.8 out of 10, Exceptional, (6)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
The price is HK$576
HK$988 total
includes taxes & fees
3 Nov - 4 Nov
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
The Wadsworth in National Historic District of Madison, Indiana.
Fridge, microwave, oven, stovetop

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (58)
"Super cute and great location"
The Wadsworth in National Historic District of Madison, Indiana.
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!
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, (9)
"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
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

Belterra Casino Resort

Belterra Casino Resort

10/10 Excellent
"Nice property, staff and rooms. Would definitely stay here again. "
David 1-night trip
Posted 5 days ago
Belterra Casino Resort