Madison vacation rentals

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Top-rated vacation rentals in Madison

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Guest favorite

Apartment in Madison

4.99 out of 5 average rating, 204 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

Guest favorite

Apartment in Madison

5.0 out of 5 average rating, 273 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”.

Guest favorite

Townhouse in Madison

4.99 out of 5 average rating, 161 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.

Guest favorite

Loft in Madison

4.85 out of 5 average rating, 281 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.

Guest favorite

Yurt in Madison

4.96 out of 5 average rating, 171 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.

Guest favorite

Guesthouse in Madison

4.99 out of 5 average rating, 225 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!

Guest favorite

Home in Madison

4.99 out of 5 average rating, 457 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

Guest favorite

Cottage in Madison

4.93 out of 5 average rating, 140 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.

Guest favorite

Home in Madison

4.98 out of 5 average rating, 135 reviews

The Crafty Fox Den - Retreat House

Nestled in Madison, Indiana’s beautiful historic district. The home is a newly renovated four square craftsman, located in the middle of town, still quiet and cozy. You are a half of a block from Main Street, the beautiful Broadway fountain, and just three blocks from the river, Lanier Mansion, and Crystal Beach, Visitor’s Center and within walking distance of all of Madison’s event locations as well as historic properties.

Guest favorite

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.

Guest favorite

Cabin in Madison

4.99 out of 5 average rating, 120 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.

Guest favorite

Home in Madison

5.0 out of 5 average rating, 107 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

Popular amenities for Madison vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Madison's top sights

The Red Pepperoni26 locals recommend

Hinkle's Sandwich Shop17 locals recommend

Kroger6 locals recommend

Key West Shrimp House8 locals recommend

Off Broadway Tap Room20 locals recommend

Bicentennial Park3 locals recommend

Other great vacation rentals in Madison

Guest favorite

Cottage in Madison

4.88 out of 5 average rating, 348 reviews

The Cozy Cottage on Main

Guest favorite

Home in Milton

4.9 out of 5 average rating, 146 reviews

Milton Hillton. River front home near Madison.

Guest favorite

Home in Bedford

4.99 out of 5 average rating, 188 reviews

Atoka Farms

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 289 reviews

The Coop

Guest favorite

Guesthouse in Madison

4.94 out of 5 average rating, 53 reviews

Studio apartment above Garage in downtown Madison

Guest favorite

Home in Madison

5.0 out of 5 average rating, 30 reviews

The Book Haven - A Book Lover's getaway near Main

Guest favorite

Home in Madison

5.0 out of 5 average rating, 14 reviews

Cabin in the Holler

Guest favorite

Apartment in Madison

4.98 out of 5 average rating, 42 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

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Other great vacation rentals in Madison

Guest favorite

Home in Deputy

5.0 out of 5 average rating, 18 reviews

The Cottage by the Woods

Guest favorite

Home in Madison

4.97 out of 5 average rating, 62 reviews

Lavender House

Guest favorite

Loft in Madison

4.92 out of 5 average rating, 85 reviews

The Atlas

Guest favorite

Guesthouse in Madison

4.91 out of 5 average rating, 67 reviews

The Goataway

Guest favorite

Home in Vevay

4.93 out of 5 average rating, 55 reviews

Riverside cottage sleeps 4

Guest favorite

Home in Madison

4.94 out of 5 average rating, 33 reviews

Your Madison Home Away from Home

Guest favorite

Home in Madison

4.93 out of 5 average rating, 76 reviews

Lanier View ll (Perfect for Social Distancing)

Guest favorite

Home in Madison

5.0 out of 5 average rating, 28 reviews

Old Winter's Saloon BNB

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Quick stats about vacation rentals in Madison

Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
6.7K reviews

Frequently Asked Questions

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 vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 50 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Madison?
Experience the best of Madison with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Madison have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Madison?
Madison has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Madison have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

Madison vacation rentals

Top-rated vacation rentals in Madison

Vacation rentals for every style

Cabins

Houses

Hotels

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Other great vacation rentals in Madison

Cottage in Madison

Home in Milton

Home in Bedford

Farm stay in Goshen

Guesthouse in Madison

Home in Madison

Home in Madison

Apartment in Madison

Other great vacation rentals in Madison

Home in Deputy

Home in Madison

Loft in Madison

Guesthouse in Madison

Home in Vevay

Home in Madison

Home in Madison

Home in Madison

Quick stats about vacation rentals in Madison

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Madison?

Are there vacation rentals with a dedicated workspace in Madison?

How much does it cost to stay in house rentals in Madison?

Do apartment rentals in Madison have air conditioning?

Are there family-friendly house rentals in Madison?

Do apartment rentals in Madison have wifi?

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