Madison Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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 $291
CA $599 total
includes taxes & fees
Nov 10 - Nov 11
207 King Suites, River Views, Deck, Downtown
A cozy room with a bed, a chair, a sofa, and a small table.

2. 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 $132
CA $237 total
includes taxes & fees
Nov 11 - Nov 12
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

3. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is CA $88
CA $156 total
includes taxes & fees
Nov 10 - Nov 11
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A modern living room with a gray sofa, wooden dining table, and chairs. A staircase leads to the upper floor, and a wooden cabinet is visible in the corner.

4. #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 $291
CA $626 total
includes taxes & fees
Nov 10 - Nov 11
#209 Kings, River View, Deck, Bicentennial Park
A covered porch with a wooden door, potted plants, and a metal railing.

5. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Lovely! We really enjoyed this amazing house!"
United States
Roxann W.
The price is CA $194
CA $340 total
includes taxes & fees
Nov 10 - Nov 11
The Artist’s A-Frame
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

6. 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 $184
CA $363 total
includes taxes & fees
Nov 10 - Nov 11
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Property grounds

7. 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 $126
CA $229 total
includes taxes & fees
Nov 10 - Nov 11
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
An outdoor patio with a hot tub, a fire pit, and string lights.

8. "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, (19 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 $206
CA $523 total
includes taxes & fees
Nov 10 - Nov 11
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
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, (3 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 $271
CA $450 total
includes taxes & fees
Nov 10 - Nov 11
Downtown Riverfront Cottage
A modern living room with a fireplace, a flat-screen TV mounted above it, and a staircase with wooden steps.

10. 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, (2 reviews)
"A perfect place to stay to explore the town of Madison! The location is within walking distance to everything you need."
United States
Claire Y.
The price is CA $210
CA $424 total
includes taxes & fees
Nov 10 - Nov 11
NEW! Historic, Walk to Main St, King Suites, Patio
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

11. 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 $191
CA $335 total
includes taxes & fees
Nov 15 - Nov 16
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A dining area with a wooden table and chairs, a vase with flowers, and a hanging light fixture.

12. 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 $184
CA $344 total
includes taxes & fees
Nov 15 - Nov 16
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
A wooden cabin with a porch, a staircase, and a deck.

13. 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 $122
CA $217 total
includes taxes & fees
Dec 8 - Dec 9
Sassafras Woodland Cabin at Lost Trails
An outdoor patio with a hot tub, a fire pit, and string lights.

14. 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 $434
CA $984 total
includes taxes & fees
Nov 16 - Nov 17
Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
A modern kitchen with white cabinetry, a granite island, stainless steel appliances, and a hanging light fixture.

15. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison Historic District
10.0 out of 10, Exceptional, (32 reviews)
"Great stay and beautiful house. The location was really outstanding and many restaurants, boutiques, and coffee shops were within walking distance. "
United States
Stephanie B.
The price is CA $444
CA $960 total
includes taxes & fees
Nov 10 - Nov 11
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

16. 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.
The price is CA $177
CA $338 total
includes taxes & fees
Nov 15 - Nov 16
Stoney Creek - Sit back and unwind
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

17. 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 $141
CA $241 total
includes taxes & fees
Nov 10 - Nov 11
Mulberry Secluded Cabin at Lost Trails
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, (80 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 $170
CA $312 total
includes taxes & fees
Nov 16 - Nov 17
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 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 $205
CA $522 total
includes taxes & fees
Nov 17 - Nov 18
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
A wooden deck with wicker furniture and a ceiling fan.

20. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (32 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is CA $155
CA $249 total
includes taxes & fees
Nov 10 - Nov 11
Cedar Rustic 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 $87 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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