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Holiday rentals in Madison

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Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Madison
The Artist’s A-Frame
Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs with complimentary Sling TV app includes 45 channels •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill
$158 SGD per night
Guest house in Madison
Mulberry Cottage In The Heart Of Downtown Madison
This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!
$136 SGD per night
Cottage in Madison
Cozy Farmhouse Retreat in Historic District
Located in the historic district in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings Madison is famous for. Three blocks from the mighty Ohio. A short five-minute drive from Clifty Falls State Park. We fell in love with Madison and know you will, too.
$134 SGD per night

Stay near Madison's top sights

Photo of Hinkle's Sandwich Shop
Hinkle's Sandwich Shop17 locals recommend
Photo of The Red Pepperoni
The Red Pepperoni26 locals recommend
Photo of Key West Shrimp House
Key West Shrimp House9 locals recommend
Photo of Bicentennial Park
Bicentennial Park3 locals recommend
Photo of Shipley's Tavern
Shipley's Tavern14 locals recommend
Photo of Off Broadway Tap Room
Off Broadway Tap Room20 locals recommend

Other great holiday rentals in Madison

Rental unit in Madison
Mad River Suites—Suite #2
$131 SGD per night
Home in Madison
Walk to the River & Main Street. 2 blocks to both!
$169 SGD per night
Rental unit in Madison
Stablemaster’s Quarters/ Best downtown location!
$209 SGD per night
Hotel room in Madison
Sunset on Broadway Suite 205 at The Chandler Hotel
$202 SGD per night
Loft in Madison
Historic Madison Spa Retreat perfect location
$127 SGD per night
Rental unit in Madison
Dragonfly Suite
$125 SGD per night
Cabin in Madison
Cabin on the Ridge: The Sequel
$180 SGD per night
Tiny home in Madison
$138 SGD per night
Townhouse in Madison
Cozy downtown home with patio walk to everything.
$154 SGD per night
Home in Madison
Charming shotgun in the heart of downtown Madison
$125 SGD per night
Cottage in Madison
Cottage*historic Madison *Pets*Trails*Clean
$126 SGD per night
Place to stay in Madison
The Riverside Retreat
$135 SGD per night

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  5. Madison