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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, 217 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

Home in Burlington

4.99 out of 5 average rating, 158 reviews

Kick Back Watching The River Go By

Great value kicking back watching the river go by. Water views are everywhere at your pet friendly 5-acre riverfront retreat and unique country vacation home. Private trails and outdoor spaces are an ideal place to spread out for relaxation and recreation. Foodies will delight with a well-appointed main kitchen and a second covered patio grilling kitchen. With family and friends, explore the many popular activities and attractions nearby, then catch a sunset next to the riverbank bonfire.

Home in Madison

4.97 out of 5 average rating, 37 reviews

The Nature House

Historic home located in downtown Madison. Walking distance to all the shops, dining, and riverfront. The house is clean and beautifully decorated. Perfect for couples or groups. Modern kitchen with all the amenities you will need. Beautiful deck and patio out back with comfortable furniture and a fully fenced yard. The decor was inspired by Mother Nature and each room is decorated with gorgeous animal prints. Three bedrooms with comfortable mattresses and an office with a convertible couch.

Cabin in Henryville

4.96 out of 5 average rating, 299 reviews

Stone Creek Cabin Retreat

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Townhouse in Madison

4.99 out of 5 average rating, 191 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, 674 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, 239 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

4.9 out of 5 average rating, 168 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 Milton

4.9 out of 5 average rating, 155 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, 152 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 Dillsboro

4.97 out of 5 average rating, 149 reviews

Spacious home in a quaint small town setting

This is a 1888 Victorian style two story brick house set in a neighborhood of older homes. Newly renovated with a fully equipped kitchen, laundry facility, dining room, living room, bedroom and 1 1/2 bathrooms on first floor. The second floor has three bedrooms and 2 full bathrooms. Each upstairs bedroom has a Smart TV and the living room has a Smart TV. It has a pleasant back yard with outdoor sitting and onsite parking.

Home in Madison

4.97 out of 5 average rating, 145 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

Home in Madison

4.98 out of 5 average rating, 43 reviews

Cabin in the Holler

Home in Aurora

4.89 out of 5 average rating, 47 reviews

Unique Luxury Family Retreat

Home in Madison

5 out of 5 average rating, 79 reviews

The Row House

Cottage in Petersburg

4.93 out of 5 average rating, 124 reviews

Rivertown Ranch near Creation Museum/Ark Encounter

Farm stay in Pendleton

4.98 out of 5 average rating, 129 reviews

Fossil Creek Woodlands...Rustic, Private, Retreat

Cabin in Rising Sun

4.91 out of 5 average rating, 55 reviews

Rustic Frontier Cabin and Grace Woods

Home in Vevay

4.96 out of 5 average rating, 157 reviews

Secluded Country Home in Historic Hoosier Hills

Cabin in Pendleton

4.94 out of 5 average rating, 33 reviews

A Little Piece of Heaven

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

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 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 $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.

Destinations to explore