Apartment vacation 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, have a coffee shop right across the street, and a flower shop beneath you! 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!

Value · Family · Comfort

The Madison Inn, Est 1925 Historic suite 107

Discover the charm of Madison from our Est 1925 Historic Overlook Suite 107. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy modern amenities such as a fully equipped kitchen, and laundry facilities to make your stay as comfortable as possible. Immerse yourself in the rich history and vibrant culture of Madison with this delightful retreat as your base. We are conveniently located close to all of the local attractions.

Location · Value · Quiet

Backstage Loft, Downtown Madison | Sleeps 4

Backstage Loft - Press Play & Unwind 🎶 Located in the heart of beautiful Downtown Madison, this music inspired loft brings the vibe. The loft is located in the alley just South of Main Street, just steps away from Shipley's Tavern, Mad Paddle, Bicentennial Park, shopping, dining, & everything Madison's Main St has to offer! Spin vinyl or stream your favorite tunes on the Bluetooth-ready record player. Enjoy a space designed for comfort and style while you unwind and relax in this cozy oasis!

Location · Family · Comfort

Stablemaster’s Quarters/ Best downtown location!

Come see why the city awarded us with the “Stellar Award”, Best Place To Stay in Madison! 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, laundry room & a furnished white kitchen will all be appreciated. Yet, historic charm remains. You will soon see why the entire building has won multiple awards. Come see why US Today awarded Madison “ Best Small Town in the Midwest”.

Value · Family · Decor

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.

Family · Location · Walkability

The Book Haven Suite on Main

Want to sleep in history above our charming bookstore? Just steps from downtown's best shops, restaurants, galleries, parks, and the fun on Main Street is our stylish Book Haven Suite. With bones from 1845, this spacious 1600 sq ft 3 bed, 2 bath apartment home is located on the entire second floor! Enjoy historical features at every turn, modern amenities, English library decor, and optional 3rd floor "Craft Haven" access. (Pics are coming for all rooms, including full kitchen & dining!)

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.

Location · Value · Getting around

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.

Location · Value · Decor

Historic Delaney's Saloon- Main Floor

Built in the early 1800's, Delaney's Saloon is a renovated main floor unit with ceilings that soar! Located just one block from Ogle Park and the scenic Ohio River, you’ll be within walking distance of many local attractions including the Vevay Art Center, the Switzerland County Historical Museum, antique shops, restaurants, & bars/ lounges. Vevay is also home to Kat Von D's tulip field and VonDLand Shoes. Madison IN, Creation Museum, and The Ark are within an hour.

Location · Sleep quality · Nearby

The Madison Inn, 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.

Value · Location · Walkability

The Music Loft

If you are looking for the best downtown location you’ve found it. If you are coming for a festival you can’t beat it. This upstairs studio apartment has everything you need. The couch converts to a double bed, in addition to a queen sized bed, a kitchenette and a wet room shower. This is a one room space. Please note if you book as 2 couples there is no privacy. The loft is located above our garage and you must climb stairs to reach the loft.

Location · Getting around · Indoor spaces

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 trees. 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.

Location · Family · Cleanliness