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Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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

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Rental unit in Madison

4.99 out of 5 average rating, 215 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

Rental unit in Madison

5 out of 5 average rating, 283 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”.

Tiny home in Milton

4.83 out of 5 average rating, 98 reviews

The Rustic River Retreat.

A perfect getaway in a Brand New home. This Tiny Home was built BIG. It features 1 bedroom with Queen size mattress. The bathroom is equipped with 36” walk in shower, full size toilet, and Washer and Dryer. The Kitchen comes equipped with a cooktop stove, air fryer microwave, Blender, Keurig Coffee maker, large refrigerator, you have access to all basic kitchen needs. Living room couch converts to a full size bed. Easy River Access for kayaking and fishing. Outdoor seating and grill!

Townhouse in Madison

4.99 out of 5 average rating, 179 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.

Loft in Madison

4.85 out of 5 average rating, 293 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.

Guesthouse in Madison

4.98 out of 5 average rating, 236 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!

Home in Madison

4.99 out of 5 average rating, 472 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

Home in Milton

4.9 out of 5 average rating, 154 reviews

Milton Hillton. River front home near Madison.

Riverfront with stunning views of the Ohio River and downtown Historic Madison, IN. Located 1 mi. from Madison and 3 mi. from Clifty Falls State Park. Madison boasts a vibrant cultural district with shopping, dining, festivals, art and live music. *under reconstruction We were unfortunately hit by an F2 tornado in March that completely destroyed the pavilion. We expect this to be rebuilt by early summer. Spacious outdoor Pavillion.

Cottage in Madison

4.92 out of 5 average rating, 146 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.

Home in Madison

4.87 out of 5 average rating, 121 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.

Cabin in Madison

4.99 out of 5 average rating, 135 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.

Home in Madison

5 out of 5 average rating, 123 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Madison vacation rentals

Free parking on premises

Air conditioning

Stay near Madison's top sights

Kroger6 locals recommend

The Red Pepperoni26 locals recommend

Hinkle's Sandwich Shop17 locals recommend

Key West Shrimp House8 locals recommend

Bicentennial Park3 locals recommend

Off Broadway Tap Room20 locals recommend

Other great vacation rentals in Madison

Home in Milton

5 out of 5 average rating, 21 reviews

The Madison-Milton Cabin

Home in Madison

4.93 out of 5 average rating, 99 reviews

Cozy 3 bedroom home, steps away from Main Street

Guesthouse in Madison

4.91 out of 5 average rating, 74 reviews

The Goataway

Home in Madison

5 out of 5 average rating, 78 reviews

The Row House

Home in Madison

4.89 out of 5 average rating, 36 reviews

• Rhythm & Blues • *Golf Cart Available

Home in Hanover

4.95 out of 5 average rating, 21 reviews

The Hanover Hideaway

Cabin in Madison

4.99 out of 5 average rating, 86 reviews

Wolf Creek Cabin

Home in Madison

4.95 out of 5 average rating, 21 reviews

Carpet Alley

Quick stats about vacation rentals in Madison

Total rentals
110 properties
Total number of reviews
7.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Madison?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in Madison?
Experience the best of Madison with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Madison have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Madison?
Four-legged friends are welcome in Madison. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Madison?
Madison has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 60 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore