A waterfall cascading into a pool surrounded by dense forest.

Search Vacation Homes in Madison

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Madison vacation homes

1. 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 AED 316
AED 565 total
includes taxes & fees
8 Dec - 9 Dec
Sassafras Woodland Cabin at Lost Trails

2. 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.
207 King Suites, River Views, Deck, Downtown

3. 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 AED 479
AED 893 total
includes taxes & fees
10 Nov - 11 Nov
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

4. 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 AED 503
AED 885 total
includes taxes & fees
10 Nov - 11 Nov
The Artist’s A-Frame

5. 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 AED 441
AED 845 total
includes taxes & fees
16 Nov - 17 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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 AED 479
AED 940 total
includes taxes & fees
10 Nov - 11 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

7. 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 AED 545
AED 1,099 total
includes taxes & fees
10 Nov - 11 Nov
NEW! Historic, Walk to Main St, King Suites, Patio

8. "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 AED 533
AED 1,293 total
includes taxes & fees
17 Nov - 18 Nov
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

9. "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.
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

10. 3BR Home Near Hanover College & Madison

3BR Home Near Hanover College & Madison
Hanover
The price is AED 808
AED 1,584 total
includes taxes & fees
15 Nov - 16 Nov
3BR Home Near Hanover College & Madison

11. 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 AED 1,129
AED 2,557 total
includes taxes & fees
16 Nov - 17 Nov
Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16

12. 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
Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio

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

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

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.4 out of 10, Exceptional, (8 reviews)
"It was lovely!"
United States
Carolyne R.
The price is AED 744
AED 1,658 total
includes taxes & fees
22 Nov - 23 Nov
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

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

16. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful view of the river! Nice location and easy to find. Highly recommend for a group getaway. "
United States
Beverly L.
The price is AED 841
AED 1,503 total
includes taxes & fees
30 Nov - 1 Dec
T&E Riverhouse Retreat

17. The River View at Esther’s

The River View at Esther’s
Vevay
10.0 out of 10, Exceptional, (3 reviews)
"This is a beautiful property and lovely house. We really enjoyed the back deck and the chairs by the river. It was nice having an enclosed yard space for our dog. The coffee station was well stocked and loved the flavored Crave pods! The bed was also very comfortable. We saw some eagles diving at possibly a muskrat. The host was quickly responsive when we reached out for a very minor issue. Thank you for a wonderful stay. Shari and Jim"
United States
James F.
The price is AED 413
AED 759 total
includes taxes & fees
5 Dec - 6 Dec
The River View at Esther’s

18. Cottage At Brianza Gardens And Winery

Cottage At Brianza Gardens And Winery
Crittenden
9.8 out of 10, Exceptional, (92 reviews)
"Nice accommodations in a beautiful setting. Very friendly host."
United States
Anonymous traveler
The price is AED 694
AED 1,127 total
includes taxes & fees
10 Nov - 11 Nov
Cottage At Brianza Gardens And Winery

19. Crittenden Ark Haven

Crittenden Ark Haven
4.5 star property
Crittenden
9.0 out of 10, Wonderful, (2 reviews)
"We recommend it to 💯"
Mexico
Greiby
The price is AED 723
AED 2,056 total
includes taxes & fees
29 Nov - 30 Nov
Crittenden Ark Haven

20. Minutes from the Ark Encounter!

Minutes from the Ark Encounter!
Dry Ridge
9.6 out of 10, Exceptional, (68 reviews)
"Fantastic host and very nice property in a quiet area!"
United States
Michelle C.
The price is AED 547
AED 1,097 total
includes taxes & fees
9 Dec - 10 Dec
Minutes from the Ark Encounter!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison Hotel Reviews