Kid-friendly vacation rentals in Jefferson County

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Top-rated kid-friendly rentals in Jefferson County

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

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

Guest favorite

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”.

Guest favorite

Home in Madison

4.98 out of 5 average rating, 105 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.

Guest favorite

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.

Guest favorite

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.

Guest favorite

Loft in Madison

4.85 out of 5 average rating, 311 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

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!

Guest favorite

Home in Madison

4.99 out of 5 average rating, 501 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

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.

Guest favorite

Home in Madison

4.91 out of 5 average rating, 205 reviews

Rivertown Retreat in Historic Downtown

Located in beautiful, historic downtown Madison! Lisa and Richard co-own and co-host this adorable, recently updated Rivertown Retreat from the 1850s. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings Madison is famous for. Three blocks from the mighty Ohio. A short five-minute drive from Clifty Falls State Park. We fell in love with Madison and know you will, too.

Guest favorite

Home in Madison

4.86 out of 5 average rating, 134 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, 156 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.