Family-friendly vacation rentals in Jefferson County

Studio apartment above Garage in downtown Madison

This special place is located in downtown Madison. It's steps from restaurants and walking distance across all of downtown Madison. This above the garage apartment overlooks a koi pond and beautiful backyard of one of Madison's historic homes. Enjoy the beautiful balcony views and relax in this studio efficiency apartment with a pull out couch. Walking distance to gorgeous hiking destinations, including Clifty Falls State Park and the Heritage Trail. Come enjoy all that Madison has to offer!

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.

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

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

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

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.

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.

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.

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.

Campus Cottage: Cozy, Convenient, Captivating

Charming ranch home on the edge of Hanover College campus. This 2 bed, 1 bath home contains hardwood flooring throughout, an eat-in dining area, open-concept living, and brand new furnishings. Explore the beauty of Hanover, just blocks from breathtaking Ohio River views, and 6 miles from Historic Downtown Madison.

Cabin in the Holler

Keep it simple at this peaceful and centrally-located cabin. Disconnect from hectic life and enjoy this slice of nature. Beautiful scenery, with a creek. We are centrally located and close to Belterra casino, Versailles park, Clifty falls, and the quaint town of historical Madison.

Dragonfly Suite -Bohemian Decor-

My home was built in 1863. It is cozy and perfect for a couple wanting to visit Historic Madison. I am located one block from Main Street in downtown Madison. Please be aware that the stairs leading up to the bed and bath are steep as shown in the pictures.