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Our top choices for Madison holiday homes
1. Sassafras Woodland Cabin at Lost Trails
Sassafras Woodland Cabin at Lost TrailsMadison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
Carrie M.
The price is £120
includes taxes & fees
7 Dec - 8 Dec
2. 207 King Suites, River Views, Deck, Downtown
207 King Suites, River Views, Deck, DowntownMadison 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. "
Matt C.
The price is £313
includes taxes & fees
9 Nov - 10 Nov
3. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio RiverMadison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
Leslie W.
The price is £184
includes taxes & fees
9 Nov - 10 Nov
4. The Artist’s A-Frame
The Artist’s A-FrameMadison
10.0 out of 10, Exceptional, (42 reviews)
"Lovely! We really enjoyed this amazing house!"
Roxann W.
The price is £179
includes taxes & fees
9 Nov - 10 Nov
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, (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."
Kyle A.
The price is £165
includes taxes & fees
8 Nov - 9 Nov
6. NEW! Historic, Walk to Main St, King Suites, Patio
NEW! Historic, Walk to Main St, King Suites, PatioMadison 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."
Claire Y.
The price is £224
includes taxes & fees
8 Nov - 9 Nov
7. 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!"
Linda G.
The price is £192
includes taxes & fees
9 Nov - 10 Nov
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 8Madison 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."
George S.
The price is £265
includes taxes & fees
17 Nov - 18 Nov
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 8Madison 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."
Norris F.
The price is £272
includes taxes & fees
9 Nov - 10 Nov
10. 3BR Home Near Hanover College & Madison
3BR Home Near Hanover College & MadisonHanover
The price is £323
includes taxes & fees
19 Nov - 20 Nov
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 16Madison Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great house. Quiet location. Easy walk to main street resturanrs and shops."
christine g.
The price is £519
includes taxes & fees
18 Nov - 19 Nov
12. #209 Kings, River View, Deck, Bicentennial Park
#209 Kings, River View, Deck, Bicentennial ParkMadison 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. "
Hannah M.
The price is £326
includes taxes & fees
9 Nov - 10 Nov
13. Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio
Christmas on Main! Luxury Stay above Main Street-Private Rooftop PatioMadison Historic District
The price is £204
includes taxes & fees
9 Nov - 10 Nov
14. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main StMadison 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. "
Stephanie B.
The price is £503
includes taxes & fees
9 Nov - 10 Nov
15. The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown MadisonHanover
9.4 out of 10, Exceptional, (8 reviews)
"It was lovely!"
Carolyne R.
The price is £355
includes taxes & fees
6 Dec - 7 Dec
16. T&E Riverhouse Retreat
T&E Riverhouse RetreatHanover
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. "
Beverly L.
The price is £293
includes taxes & fees
17 Nov - 18 Nov
17. The River View at Esther’s
The River View at Esther’sVevay
10.0 out of 10, Exceptional, (2 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"
James F.
The price is £155
includes taxes & fees
9 Nov - 10 Nov
18. Cottage At Brianza Gardens And Winery
Cottage At Brianza Gardens And WineryCrittenden
9.8 out of 10, Exceptional, (92 reviews)
"Nice accommodations in a beautiful setting. Very friendly host."
Anonymous traveller
The price is £231
includes taxes & fees
9 Nov - 10 Nov
19. Crittenden Ark Haven
Crittenden Ark HavenCrittenden
9.0 out of 10, Wonderful, (2 reviews)
"We recommend it to 💯"
Greiby
The price is £431
includes taxes & fees
29 Nov - 30 Nov
20. Serene Lake Cabin Near Ark w/ Hot Tub & Kayaks
Serene Lake Cabin Near Ark w/ Hot Tub & KayaksCrittenden
10.0 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay the place was well kept and clean. Just wished we could of stayed longer."
Eldon M.
The price is £308
includes taxes & fees
8 Nov - 9 Nov
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.
Madison and related destinations
Stroll through the Historic District, where grand homes and antique shops transport you to a bygone era. Hike scenic trails to thundering waterfalls in Clifty Falls State Park, then sample award-winning wines at local vineyards.
