Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Guest favourite

Flat in Madison

5.0 out of 5 average rating, 114 reviews

River's Edge II-Historic Hunger House-Downstairs

Newly renovated DOWNSTAIRS unit of this historic home in the heart of downtown Madison. Experience the unique blend of historic character and contemporary comfort! Relax on our front porch (complete with swing and river view) after a busy day of touring shops, historic sites, cultural, or music festivals that are the heart of Madison... WELCOME to the River's Edge II! Extended stay (wk-mo) discounts 21%-49% Rent one or both floors (See "River's Edge-UPSTAIRS-listing) SEND INQUIRY FOR PRICING.

13–20 Feb

€ 107 per night

Guest favourite

Flat in Madison

5.0 out of 5 average rating, 271 reviews

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

20–27 Nov

€ 222 per night

Guest favourite

Townhouse in Madison

4.99 out of 5 average rating, 157 reviews

Cozy downtown home with patio walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

26 Jul – 2 Aug

€ 149 per night

Guest favourite

Loft in Madison

4.85 out of 5 average rating, 279 reviews

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

12–19 Jun

€ 92 per night

Guest favourite

Yurt in Madison

4.97 out of 5 average rating, 167 reviews

Madison's only Yurt experience!!!

You'll love this unique and romantic escape in the hills of southern Indiana! Located just 20 minutes from beautiful downtown Madison and Vevay. Enjoy the countryside in your very own yurt. Come relax after a hard day of shopping in downtown Madison or after a late night at Belterra casino. You will love the warm inviting boho style of decor while enjoy the beautiful sunsets from the deck. The stars look so close you could touch them from the grassy hillsides of this enchanting property.

4–11 Jan

€ 186 per night

Guest favourite

Guest house in Madison

4.99 out of 5 average rating, 223 reviews

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!

8–15 Jul

€ 121 per night

Guest favourite

Cottage in Madison

4.88 out of 5 average rating, 348 reviews

The Cozy Cottage on Main

This quaint and cozy home sits on Main Street in “Historic Downtown” Madison, Indiana. It’s location is close to Clifty Falls State Park entrance, and a short walk to the Ohio River. “The Cozy Cottage on Main" was built in the 1940’s. The primitive decor makes you feel like your staying at grandmas house. The nostalgia the Cozy Cottage creates will bring back old memories and compliments the history of the area. It is perfect for a couples, girls or honeymoon getaway!

14–21 Sep

€ 157 per night

Guest favourite

Home in Madison

4.99 out of 5 average rating, 453 reviews

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 •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

29 Jan – 5 Feb

€ 139 per night

Guest favourite

Cottage in Madison

4.93 out of 5 average rating, 139 reviews

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 for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

9–16 Oct

€ 105 per night

Guest favourite

Home in Madison

4.88 out of 5 average rating, 114 reviews

Carole's Cottage

Quaint cottage located in downtown Madison. A short walk to all shops & restaurants and beautiful riverfront. Guests have entire home including a screened in back porch to enjoy your morning coffee or just relax and read a book. Master bedroom has a king size bed and 2nd bedroom has a futon. Our kitchen is fully equipped, including stove, refrigerator, microwave and keurig coffee maker.

19–26 Sep

€ 97 per night

Guest favourite

Cabin in Madison

4.99 out of 5 average rating, 119 reviews

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

30 Sep – 7 Oct

€ 219 per night

Guest favourite

Home in Madison

5.0 out of 5 average rating, 104 reviews

Charming shotgun in the heart of downtown Madison

This charming, stylish 2-bedroom shotgun house is located on Main Street in historic downtown Madison, IN. You'll be just steps away from locally owned shops, bars, and restaurants, and within walking distance of the Ohio River and Madison's many festivals and events. Enjoy off-street parking, modern amenities, and the perfect front-porch view.

17–24 Oct

€ 190 per night