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Jefferson County Holiday Rentals

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Top Holiday Rentals Destinations in Jefferson County

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

9.8 out of 10, Exceptional, (40)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is NZ$375
includes taxes & fees
30 Sept - 1 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

2.0 star property
10.0 out of 10, Exceptional, (11)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is NZ$291
includes taxes & fees
30 Sept - 1 Oct
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

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!

10.0 out of 10, Exceptional, (46)
"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!!

9.8 out of 10, Exceptional, (19)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great old home and cool neighborhood. "
Charming 3-bedroom house in lovely downtown Madison.

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

10.0 out of 10, Exceptional, (201)
"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

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

Historic city overlook suite 206, Historic city overlook suite 306

9.4 out of 10, Exceptional, (8)
"Very clean and cozy! Nice area close to town. "
The price is NZ$315
includes taxes & fees
8 Oct - 9 Oct
Historic city overlook suite 206, Historic city overlook suite 306

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 NZ$502
includes taxes & fees
30 Sept - 1 Oct
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

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 NZ$246
includes taxes & fees
28 Oct - 29 Oct
Sunset over the city Suite 201, Sunset over the city Suite 201

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 NZ$418
includes taxes & fees
20 Oct - 21 Oct
The Artist’s A-Frame

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (94)
"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

10.0 out of 10, Exceptional, (12)
"Great one bedroom apartment! It was clean and great location for our quick getaway."
The price is NZ$395
includes taxes & fees
5 Oct - 6 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

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

9.8 out of 10, Exceptional, (6)
The price is NZ$323
includes taxes & fees
30 Sept - 1 Oct
Modern Nature Cabin | Private Escape in the Forest

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

10.0 out of 10, Exceptional, (56)
"Home was the perfect setting for our yearly girl’s get together!"
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

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

9.6 out of 10, Exceptional, (5)
"Nice new property in a great location!"
The price is NZ$217
includes taxes & fees
30 Sept - 1 Oct
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (57)
"We love the Wadsworth! It’s our home away from home when we are in Madison. As always, everything was perfect. "
The Wadsworth in National Historic District of Madison, Indiana.

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

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

Everything you need to know about Jefferson County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jefferson County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jefferson County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jefferson County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jefferson County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jefferson County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jefferson County holiday rentals we have selected for you start as low as NZ$217 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jefferson County rentals

At Expedia, we put the best Jefferson County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jefferson County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jefferson County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jefferson County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.