Madison Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Madison vacation rentals

A dining area with a wooden table set for six, surrounded by chairs.

1. 207 King Suites, River Views, Deck, Downtown

207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (48 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is CA $288
CA $592 total
includes taxes & fees
Nov 10 - Nov 11
207 King Suites, River Views, Deck, Downtown
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

2. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is CA $86
CA $154 total
includes taxes & fees
Nov 16 - Nov 17
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A cozy room with a bed, a chair, a sofa, and a small table.

3. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is CA $131
CA $234 total
includes taxes & fees
Nov 9 - Nov 10
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden cabin with a porch, a staircase, and a deck.

4. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is CA $126
CA $222 total
includes taxes & fees
Dec 7 - Dec 8
Sassafras Woodland Cabin at Lost Trails
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

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

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (52 reviews)
"Had a very nice stay"
United States
Brad P.
The price is CA $170
CA $308 total
includes taxes & fees
Nov 9 - Nov 10
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Property grounds

6. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (20 reviews)
"Clean and cozy"
United States
Julie
The price is CA $125
CA $227 total
includes taxes & fees
Nov 10 - Nov 11
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered porch with a wooden door, potted plants, and a metal railing.

7. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Great experience. Definitely recommend staying here if you’re visiting Madison. Great location to down town,"
United States
Mike H.
The price is CA $191
CA $337 total
includes taxes & fees
Nov 10 - Nov 11
The Artist’s A-Frame
A modern living room with a fireplace, a flat-screen TV mounted above it, and a staircase with wooden steps.

8. NEW! Historic, Walk to Main St, King Suites, Patio

NEW! Historic, Walk to Main St, King Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
The price is CA $207
CA $420 total
includes taxes & fees
Nov 10 - Nov 11
NEW! Historic, Walk to Main St, King Suites, Patio
A dining area with a view of a bridge over a river, a table set with plates and cutlery, and a potted plant on the windowsill.

9. Downtown Riverfront Cottage

Downtown Riverfront Cottage
Madison Historic District
10.0 out of 10, Exceptional, (2 reviews)
"House was very nice, very clean. The view of the river was magnificent. Next little getaway we would return again"
United States
Curtis M.
The price is CA $268
CA $466 total
includes taxes & fees
Nov 10 - Nov 11
Downtown Riverfront Cottage
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

10. The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (55 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is CA $182
CA $359 total
includes taxes & fees
Nov 8 - Nov 9
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A dining area with a wooden table and chairs, a vase with flowers, and a hanging light fixture.

11. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
United States
Leslie W.
The price is CA $183
CA $339 total
includes taxes & fees
Nov 8 - Nov 9
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

12. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (134 reviews)
"Our family enjoyed our stay."
United States
Shanna S.
Stoney Creek - Sit back and unwind
A building with a number '209' above the entrance, a dark door, and a small potted plant beside the door.

13. #209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison Historic District
10.0 out of 10, Exceptional, (73 reviews)
"The house was clean, comfortable, and had everything we needed. The location was great; very close to restaurants and shops on Main Street as well as the parks by the river. "
United States
Hannah M.
The price is CA $289
CA $621 total
includes taxes & fees
Nov 8 - Nov 9
#209 Kings, River View, Deck, Bicentennial Park
An outdoor patio with a hot tub, a fire pit, and string lights.

14. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison Historic District
10.0 out of 10, Exceptional, (22 reviews)
"This was perfect for our family of 6, the house was super clean and within walking distance to the river and many restaurants and shopping. We will definitely be staying again."
United States
George S.
The price is CA $206
CA $520 total
includes taxes & fees
Nov 18 - Nov 19
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
2

15. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is CA $140
CA $239 total
includes taxes & fees
Dec 6 - Dec 7
Maple Cozy Cabin at Lost Trails
A modern kitchen with a large island, wooden cabinets, and stainless steel appliances.

16. Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio

Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio
Madison Historic District
The price is CA $395
CA $421 total
includes taxes & fees
Nov 11 - Nov 12
Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio
An outdoor patio with a hot tub, a fire pit, and string lights.

17. Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16

Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
Madison Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great house. Quiet location. Easy walk to main street resturanrs and shops."
United States
christine g.
The price is CA $430
CA $973 total
includes taxes & fees
Nov 18 - Nov 19
Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

18. 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, (79 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 CA $158
CA $309 total
includes taxes & fees
Nov 8 - Nov 9
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
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 CA $204
CA $518 total
includes taxes & fees
Nov 18 - Nov 19
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

20. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"We loved the cabin, it had everything we needed - lovely peaceful surroundings, and was very clean! Thank you."
United States
Lisa S.
The price is CA $140
CA $239 total
includes taxes & fees
Nov 8 - Nov 9
Mulberry Secluded Cabin at Lost Trails
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 Madison Hotel Reviews

A spacious living room with a green sofa, a leather armchair, and a wooden coffee table. A brick wall and a chandelier are visible.
The Chandler Hotel

The Chandler Hotel

The Chandler Hotel
Madison Historic District

10/10 Excellent

Lovely and unique historical place turned into a hotel with a stylish touch in the inside decoration.
Canada
Zdravko
Reviewed June 9, 2025
The Chandler Hotel

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation 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 Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. 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 Madison vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison vacation rentals we have selected for you start as low as CA $81 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation 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 Madison 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 Madison vacation.

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

Frequently Asked Questions

Are there vacation rentals in Madison?

Yes, we have vacation rentals in Madison close to Madison Railroad Station Museum, or you can choose a more secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and riverfront in Madison. Allow some time to check out the shops during your trip.

What's the top vacation rental in Madison?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: Visitors like this Madison vacation home rental. It offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Madison?

Expedia has 47 vacation rentals for your stay in Madison.

What’s there to see and do in Madison?

Cultural attractions include Schofield House and Jeremiah Sullivan House, whereas Ohio River Valley and Johnson Lake are a couple of picturesque spots to enjoy the outdoors. Historic District and Francis Costigan House are other places to visit while you're in town.

What’s a vacation rental in Madison like?

Vacation rentals are private properties you can book for several days or longer in Madison. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for small groups.

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