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Madison vacation rentals

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Top-rated vacation rentals in Madison

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

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Rental unit in Madison

4.99 out of 5 average rating, 230 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, 291 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”.

Home in Madison

4.98 out of 5 average rating, 104 reviews

Riverview Historical Retreat

Come stay in newly-renovated home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison.

Loft in Madison

4.92 out of 5 average rating, 102 reviews

The Atlas

This spacious upstairs loft is located in beautiful Downtown Madison, Indiana. Our 1880's property is only 1 block from Main St. and 2 blocks to the riverfront. We are close to the Heritage Trail, scenic Vaughn Drive, wineries, brewery, antique shops, restaurants, and many more local attractions and festivals, as well as, only 4 miles from Clifty Falls State Park. This is a great place if you are looking to get away with your significant other, a girls/guys trip or taking the family hiking.

Townhouse in Madison

4.99 out of 5 average rating, 206 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.

Cabin in Madison

4.98 out of 5 average rating, 690 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Guesthouse in Madison

4.98 out of 5 average rating, 245 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!

Houseboat in Florence

4.91 out of 5 average rating, 171 reviews

Peaceful Houseboat off the Ohio River

This floating home is located in a beautiful setting in a cove off the Ohio River. Drive to nearby towns and visit antique shops and restaurants in Vevay and Madison, Indiana. Clifty Falls is a great place to hike. Beltera Casino Resort is down the street and the marina is also close to Rising Sun, Hollywood Casino, and Sunset Grill on the water in Warsaw, Kentucky. Conveniently located close to The Neeley Family Distillery. Some have visited the Ark while staying here also.

Home in Vevay

4.96 out of 5 average rating, 160 reviews

Secluded Country Home in Historic Hoosier Hills

You’ll love the property because of the private secluded location and the views. The property is good for couples, solo families (with kids), all girls/boys gatherings and big groups. The house has over 1900 square feet of living space plus a sunroom looking over the pond and woods. There are two TVs with cable connection and one tv with an antenna. One TV is in the common living area and the other tv's are in two bedrooms, Catch and release fishing is permitted.

Home in Milton

4.91 out of 5 average rating, 160 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

4.91 out of 5 average rating, 162 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

4.97 out of 5 average rating, 148 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.

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

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Madison vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Madison's top sights

Clifty Falls48 locals recommend

The Red Pepperoni26 locals recommend

Lanier Mansion State Historic Site21 locals recommend

Off Broadway Tap Room20 locals recommend

Hinkle's Sandwich Shop17 locals recommend

Thomas Family Winery17 locals recommend

Other great vacation rentals in Madison

Cottage in Madison

4.85 out of 5 average rating, 124 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Home in Madison

4.98 out of 5 average rating, 52 reviews

Cabin in the Holler

Rental unit in Madison

4.99 out of 5 average rating, 79 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

Guest suite in Hanover

5 out of 5 average rating, 66 reviews

OFF THE CLOCK River House

Farm stay in Vevay

4.96 out of 5 average rating, 54 reviews

The Bolton Ranch - The Lodge

Cabin in Madison

4.92 out of 5 average rating, 50 reviews

Historic 1830s Log Cabin in Madison, IN

Home in Madison

4.98 out of 5 average rating, 64 reviews

Main Street - Heart of downtown Madison!

Guesthouse in Madison

4.91 out of 5 average rating, 82 reviews

The Goataway

Quick stats about vacation rentals in Madison

Total rentals
130 properties
Total number of reviews
7.4K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
120 properties include access to wifi

Frequently Asked Questions

Are there pet-friendly vacation rentals in Madison?
Four-legged friends are welcome in Madison. Choose from more than 30 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 60 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 $30 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 20 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 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Madison have wifi?
Absolutely! We offer over 60 house rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore