Apartment holiday rentals in Madison

The Main St. Oasis - Heart of Downtown Madison

Welcome to the Main St. Oasis in the heart of Historic Downtown Madison! We're steps away from Lanthier Winery, shopping, fine dining, the Ohio River, a bakery underneath the apt & have a coffee shop right across the street. Close to Clifty Falls State Park (3 min) & Hanover College (9 min). Enjoy a unique retro-western theme, with games & luxuries for all ages. Perfect for couples, families, or small groups. Ideal for exploring Madison’s top attractions or relaxing in comfort right on Main St!

Livery Loft: BEST location!

This beautiful loft apt is spacious and guests say "it's beyond amazing"! 2+ bdrm 2 luxury bathrooms offer SO many amenities you won't want to leave! It has a very spacious living room, dining room & gourmet kitchen. The master bath has a fireplace above the soaking tub & a massage shower. The other bath has a rainfall shower and heated toilet seat: add luxury linens & you will feel very pampered! We have the best location just off main street and 3 blocks from the relaxing riverwalk.

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”.

The Regatta Room (Unit 3) - Ohio River Views

Welcome to The Regatta Room by Parker Places! This luxury studio suite is recently remodeled and features brand new everything. It comes stocked with a full eat-in kitchen, new appliances, one queen-size bed, a comfy couch, TV, WiFi, and more. PRIME location with a view of the Ohio River, instant access to the walking path along the river, close to shops, cafes, & restaurants. PERFECT location for anything downtown, and it is just steps away from Madison's famous Regatta event.

Hometown on Main Street, Suite 102

Welcome to Hometown on Main, Suite 102, nestled in the heart of Madison. This cozy 1-bedroom, 1-bathroom rental is your perfect getaway, offering a blend of comfort and convenience. This room overlooks downtown Madison and is convenient to all the historic sites and local dining. Enjoy your morning coffee while overlooking downtown Main Street. Immerse yourself in the charm of Madison while enjoying the comforts of home. Ideal travelers or couples seeking a serene retreat.

Sunset over the city Suite 201

Discover the charm of Madison from our cozy suite, "Sunset over the City" Suite 201. Perfect for couples or solo travelers, this 1-bedroom, 1-bathroom rental offers a beautiful view of Historic downtown Madison. Enjoy modern conveniences like a full kitchen for your culinary adventures, laundry facilities, and all the essentials. Located in the heart of Madison, you're perfectly positioned to explore the city's delights. Don't miss the breathtaking sunsets.

Delaney's Saloon

Originally Delaney's Saloon in the early 1800s is now your home away from home. A labor of love that I can't wait to share with you! I bought this beautiful, historic building in early 2023 and renovated from the floor and up. A washer and dryer is on site and the kitchen is fully equipped. I want you to feel at home and need nothing during your stay. But, if I have forgot something, I'm easily accessible if needed, living just a few blocks away.

Charolotte's Corner Overlook, Suite 101

Experience beautiful Mornings in this Corner suite. Rest with a beautiful view of Downtown or enjoy a peaceful stroll down Main Street. This suite is located right on Main Street a eating area, and is a great place for resting and relaxation. If you're looking for a local dining special. Then this room is conveniently located just a few blocks from entertainment and fine dining. This cozy suite is in the heart of Historic Madison.

Warren’s Guest Cottage

Apartment located in downtown Historic Madison, Indiana, near Ohio river. Within walking distance of Main Street to the north with restaurants and retail stores and the Ohio River to the south where you can run, walk or just sat and relax on the river walk and enjoy the views of the river and it’s travel. Off street parking with private entrance.