You'll be close to everything when you stay at this conveniently located historical duplex. All modern amenities are included to make your stay pleasant. Your stay includes: galley kitchen, Wifi , washer & dryer, back patio with seating and grill. Recently renovated down to the bones, the Historic "Stevenson" home was owned by Sarah, the daughter of John Paul, a key founder of Madison. Two blocks from Main St., three blocks from the Lanier Mansion, Riverfront, Heritage Trail, and shopping. The space The kitchen, living room/dining room combo, and bathroom/laundry room are down stairs. Upstairs are the bedrooms. There’s a paved patio outback with a grill and seating, and some chairs out on the front porch. There’s enough off street parking for 2 cars per unit down the alley behind the home, and street parking out front. Guest access You can use the whole side that you rented, both inside and out. Other things to note *Both bedrooms are upstairs, the bathroom is down stairs. *handrail is illuminated for safety and does not turn off. *there is a 34” corner shower, no tub *no evs (electric vehicles) or electric golf carts are to be plugged in

"Silverwood" Historic 1850s Duplex, sleeps 6

You'll be close to everything when you stay at this conveniently located historical duplex. All modern amenities are included to make your stay pleasant. Your stay includes: galley kitchen, Wifi , washer & dryer, back patio with seating and grill. Recently renovated down to the bones, the Historic "Stevenson" home was owned by Sarah, the daughter of John Paul, a key founder of Madison. Two blocks from Main St., three blocks from the Lanier Mansion, Riverfront, Heritage Trail, and shopping. The space The kitchen, living room/dining room combo, and bathroom/laundry room are down stairs. Upstairs are the bedrooms. There’s a paved patio outback with a grill and seating, and some chairs out on the front porch. There’s enough off street parking for 2 cars per unit down the alley behind the home, and street parking out front. Guest access The whole side you’ve rented, both inside and outside. Other things to note *Both bedrooms are upstairs, the bathroom is down stairs. *handrail is illuminated for safety and does not turn off. *there is a 34” corner shower, no tub *no evs (electric vehicles) or electric golf carts are to be plugged in

"Abercrombie" 1850s Duplex, Sleeps 6

The Daisy house located in the heart of downtown Madison Indiana, just steps from Main Street. Walking distance from restaurants and shops. Very spacious! Featuring two queen size beds, a couch that folds down into a single bed and a single roll away bed. One bathroom. Washer and dryer in house. Also features a small deck with yard. Private parking space behind the house with room for two cars. Self check in with smart lock. The space Two bedrooms upstairs, fold out single sofa and single roll away bed main floor.Bathroom on main floor off kitchen. Washer and dryer located in bathroom. Other things to note There is a six guest limit. Contact the host with additional questions

The Daisy House, a cheerful two bedroom townhouse

THE AVIATOR - where historic character meets modern comfort. Built in 1901, this beautifully restored apartment offers the perfect stay for families, couples, or small groups looking to experience the heart of Madison, Indiana. During its restoration, we kept original elements like tall ceilings and large rooms, while thoughtfully updating the layout. The result is a warm, inviting space that honors its past without sacrificing comfort. The space A Heritage Hideaway in Madison Indiana. Rich in history, elevated by modern design, 'THE AVIATOR" is a beautifully restored 1901 apartment that blends timeless character with today’s comforts. Whether you’re here for a relaxing escape or a weekend of local adventures, this thoughtfully curated space offers the perfect backdrop for your stay in Madison, Indiana—one of America’s most picturesque river towns. 🕰 Historic Elegance, Thoughtfully Preserved Built in 1901, this home has seen more than a century of Madison’s story unfold. After surviving a fire decades ago, the home was carefully rebuilt to preserve its original form—while enhancing it with tasteful modern updates. You’ll love: Towering ceilings and rich woodwork Large, light-filled rooms with tall windows Original architectural details blended with curated local artwork Cozy reading nooks and beautiful textures throughout A perfect balance of history, charm, and comfort 🛌 Sleep, Soak, and Stay Awhile Designed for relaxation and connection, The Aviator comfortably accommodates up to 6 guests, offering: 2 spacious bedrooms with 3 inviting beds Updated bathrooms with spa-like features A fully equipped kitchen for cooking or warming up local favorites A serene tea nook—ideal for morning coffee, journaling, or reading Thoughtful amenities to help you feel right at home 🐾 Dog-Friendly + Kid-Approved We believe travel should be joyful and stress-free for everyone—including your furry friends and little ones. The Aviator is: Pet-friendly with space and comfort for your dog Kid-friendly, making it a great option for families 🚶‍♀️ Walk Everywhere – Unbeatable Downtown Location Located in the heart of Madison’s historic district, The Aviator puts you within walking distance of the town’s best sights and experiences: The Broadway Fountain – Madison’s most photographed landmark Crystal Beach – A charming seasonal public pool Ohio River Bridge & Waterfront – Ideal for sunset strolls and river views Shops, cafés, wine bars, and bakeries just around the corner Historic homes and local walking tours to explore Madison’s rich heritage From here, you can park once and forget the car—everything you need is just steps away. The Aviator isn’t just a place to stay—it’s a launchpad for soaking in the stories, beauty, and charm of Madison, Indiana. We can't wait to host you.

The Aviator: Serene Ambience & Stylish Comfort

Located just steps from shops, restaurants, the riverfront, and the walking bridge, our apartment offers convenience and character. Nestled in a preserved building that's over a century old, this updated space combines timeless architectural charm with modern amenities to give you a comfortable and memorable stay. Whether you're exploring Clifty Falls State Park, visiting loved ones at Hanover College, or simply soaking in the local culture, you'll find everything you need just moments away. The space Both bedrooms include a queen bed, a wardrobe stocked with hangers for unpacking, and plenty of space to move around and be comfortable. The first bedroom also includes a twin day bed, and there's a pack-in-play available for the little one. There's one full bathroom with a shower and a washer and dryer. We've got everything you need in the way of soap, shampoo & conditioner, and laundry detergent. The living room includes a comfy sectional and Smart TV, along with a basket of games, puzzles, and kids' books. The kitchen is stocked with a fridge & freezer, oven, stove, microwave, and many small appliances including an air fryer, coffee maker, toaster, George Foreman grill, and griddle. We also have a selection of teas, coffee, cream & sugar, and many different spices. The goal is that you only have to worry about bringing the food, and you'll have everything else you need to make a tasty meal that can be enjoyed in the sunny turret dining room. Outside there's a picnic table, along with a covered porch with chairs for outdoor dining. Guest access This unit is a second floor apartment that requires guests to climb approximately 16 steps. You will have the entire apartment to yourself. Other things to note This apartment is only available Thursday-Saturday nights, aside from a few weeks throughout the year when there is additional availability.

Downtown Madison Charmer

AQUANTIS - where historic character meets modern comfort. Built in 1901, this beautifully restored apartment offers the perfect stay for families, couples, or small groups looking to experience the heart of Madison, Indiana. During its restoration, we kept original elements like tall ceilings and large rooms, while thoughtfully updating the layout. The result is a warm, inviting space that honors its past without sacrificing comfort. The space A Heritage Hideaway in Madison Indiana. Rich in history, elevated by modern design, 'AQUANTIS" is a beautifully restored 1901 apartment that blends timeless character with today’s comforts. Whether you’re here for a relaxing escape or a weekend of local adventures, this thoughtfully curated space offers the perfect backdrop for your stay in Madison, Indiana—one of America’s most picturesque river towns. 🕰 Historic Elegance, Thoughtfully Preserved Built in 1901, this home has seen more than a century of Madison’s story unfold. After surviving a fire decades ago, the home was carefully rebuilt to preserve its original form—while enhancing it with tasteful modern updates. You’ll love: Towering ceilings and rich woodwork Large, light-filled rooms with tall windows Original architectural details blended with curated local artwork Cozy reading nooks and beautiful textures throughout A perfect balance of history, charm, and comfort 🛌 Sleep, Soak, and Stay Awhile Designed for relaxation and connection, The Aquantis comfortably accommodates up to 6 guests, offering: 2 spacious bedrooms with 3 inviting beds Updated bathrooms with spa-like features A fully equipped kitchen for cooking or warming up local favorites A serene tea nook—ideal for morning coffee, journaling, or reading Thoughtful amenities to help you feel right at home 🐾 Dog-Friendly + Kid-Approved We believe travel should be joyful and stress-free for everyone—including your furry friends and little ones. The Aquantis is: Pet-friendly with space and comfort for your dog Kid-friendly, making it a great option for families 🚶‍♀️ Walk Everywhere – Unbeatable Downtown Location Located in the heart of Madison’s historic district, The Aquantis puts you within walking distance of the town’s best sights and experiences: The Broadway Fountain – Madison’s most photographed landmark Crystal Beach – A charming seasonal public pool Ohio River Bridge & Waterfront – Ideal for sunset strolls and river views Shops, cafés, wine bars, and bakeries just around the corner Historic homes and local walking tours to explore Madison’s rich heritage From here, you can park once and forget the car—everything you need is just steps away. Aquantis isn’t just a place to stay—it’s a launchpad for soaking in the stories, beauty, and charm of Madison, Indiana. We can't wait to host you.

Aquantis: Sleeps 6, Pets OK, Steps from Main St

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. The space Come and enjoy magical Madison in Lisa and Richard's home away from home! Features two spacious bedrooms with comfy beds, one with a king and one with a queen. Ample pillows and blankets. Master bedroom has cable TV; the second bedroom does not have a TV. Both bedrooms have a ceiling fan and loads of closet and drawer space. Entire house has Wifi. No stairs required to enter; our living space is all on one floor. But there is one small step to enter the master bedroom with the king size bed. The bath features a combined tub and tiled shower with a convenient built-in nook for your toiletries. And you'll appreciate the full-size washer and dryer just beyond the sliding barn doors. We supply laundry detergent, soap and, of course, toilet paper. The living room invites you to put your feet up on the coffee table and turn on the cable TV and electric fireplace while unwinding. Our fully stocked kitchen features stainless appliances and offers everything you need if you feel like cooking in -- pots, pans, and plenty of towels, dishware, water glasses, wine glasses, utensils, and seasonings. Kitchen table seats four, plus there are two bar stools at the counter island. We provide coffee and sugar/powdered creamer. Have an early morning or evening beverage on our adorable porch in the rear; there are seats for four. And you can enjoy a cozy fire in the backyard with our stone fire pit, surrounded by four chairs, each with a drink stake for your drink of choice. We provide wood for the fire pit, tongs, firestarter squares, and lighter. Let's get toasty in historic downtown Madison! Guest access All rooms are readily accessible, with the exception of the master bedroom. One small step up is required to enter. Other things to note Check in time is 3 p.m. Check out time is noon. Free street parking is ample in this residential neighborhood. Typically, you can park right in front of the house.

Rivertown Retreat in Historic Downtown

Come one, come all. This relaxing creekside home will sure give you a relaxing feel just blocks from the lively hood of Downtown Madison. Indiana. Located on the East side of downtown Madison this semi private location gives a quiet county vibe. Madison is a great little music town with over 300 blocks to explore in Historic Madison. You can find live music most every night. We also have a 4 seater golf cart we keep in the garage there. it is available for rent as well. message to inquire. The space spacious 2 bedroom home in a private location just blocks from all downtown Madison has to offer. More guests welcome if needed. Tent camping available in the side yard if you have adventurous kids or friends. Guest access entire home Other things to note more guests are welcome if needed. air mattress in the closet. musical instruments are for playing. please enjoy yourself here.

• Rhythm&Blues • *Pets welcome*Golf Cart available

Rivers Edge-Historic Hunger House-Upstairs-Madison

Enjoy all of the convenience of downtown with all of the comforts of home. This 2 bedroom, 1.5 bath home comes equipped with all of your travel essentials, including a fully stocked coffee bar. Just a short walk gets you to historical Main Street, the Broadway Fountain, and the iconic Ohio river. The space As you step up into the living room from the front door you’ll find a big comfy couch, a window seating area, a small bistro table for dining, and a smart tv. Through the French doors you’ll see the first bathroom, and a fully equipped kitchen. There is a small island with 2 barstools, and stainless steel appliances. We’ve tried to provide everything you need to be able to cook from home, if desired, and there is a grocery store just a short walk away if you choose to do so. Up the stairs you’ll find the 2 bedrooms, a bathroom with a full sized shower, and the washer and dryer. Bedroom 1 has a king sized bed, a dresser, a large closet, and a chair that pulls out into a small bed. Bedroom 2 has a queen sized bed, a closet, and a dresser. We’ve provided extra linens and pillows in each bedroom closet. Along with other amenities such as a floor fan, iron and ironing board, and a sound machine, you’ll find extra device chargers in the night stands just in case you forgot yours at home! We want your stay here to be as comfortable as possible, and we hope you enjoy the beautiful town of Madison.

The One With The Red Door

Nestled in the heart of Madison's vibrant downtown district, The Olive House has timeless charm and modern comfort. Situated just steps away from a delightful array of eateries, antique boutiques, and the Ohio River,  the Olive House comfortably accommodates up to 4 guests and the outdoor living area provides the perfect spot for relaxation. Experience the charm at The Olive House where every detail has been carefully curated to ensure a memorable stay that beckons you to return again and again.

The Olive House

This unique location is near everything, making it simple to organize your trip. The Riverstone Getaway is located in beautiful downtown Madison. Once you park your car you can walk just about everywhere or rent a golf cart to get around. You will have a beautiful view of the river, from the backyard, and your only steps from taking a stroll along the riverfront. The space Living Room Hardwood floors, a comfy futon couch, two end tables, a TV console cabinet with storage space, and you'll find games, extra chargers, and rainy-day umbrellas in case you forgot to pack your own. A smart TV is hung above the TV console. Kitchen- A cute but functional kitchen with a small island with a built-in cutting board that slides out. There is a kitchen table in the kitchen that seats four and can be used as a workstation. The Kitchen is equipped with: * stove *wine glasses			 *refrigerator *pots & pans *microwave		 *complete dish sets *baking sheets *toaster			 *eating utensils *cooking utensils *blender			 *drinking glasses *outdoor BBQ utensils *Pet feeding and watering station (be sure to tell us your furry friend is coming so we can leave them a complimentary treat bag and stuffed toy!) Complimentary coffee bar stocked with k-cup coffee, decaf coffee, hot chocolate k-cups, sugar, creamer, and tea for non-coffee drinkers. Welcome basket with salty snacks, sweet snacks, and water. First aid kit located in the medicine cabinet in the bathroom . A washer and dryer are located in the kitchen. Complimentary detergent pods and fabric sheets are provided. Lawn chairs and beach towels They are located in the closet in the living room. Outdoor entertaining area- The backyard features a cozy deck that has a relaxing view of the river, a seating area on the deck, a BBQ grill, and a wood fire pit. Bedroom 1, Features a queen-size bed, a dresser, a closet, and bedside tables with lamps. Bedroom #2, The room has a queen-size bed, a mirror, bedside tables, lamps, a rocking chair, a clothes rack to hang clothes on, and a dresser that can be used as a desk. Bathroom - The bathroom offers a shower and a vanity with a well-lit mirror. Forgot a few toiletries? No worries. We provide travel-sized toiletries such as toothpaste, toothbrushes, razors, shampoo, conditioner, and shower gel. Ladies, we provide black makeup washcloths to remove makeup at night. They are located in the bathroom for your convenience. We also provide full-size body wash, shampoo and conditioner. Guest access Guests have access to the entire house. Except for the cellar and a few cabinets. Guests will use the side door to access the house. Other things to note The lock code will be given to you 48 hours before arrival, but it will not be active until 3:00 pm when you can access the property.

The Riverstone Getaway in historical Madison, IN

🏠 This updated historic home features two bedrooms, both with king beds, and one full bathroom with a washer and dryer. The home is clean and charming, sure to be just what you need for a family trip, girls' weekend, or romantic getaway! 🚸 Enjoy a brief walk to all that downtown Madison, Indiana has to offer. It is also a quick drive to Madison's hilltop, Hanover College, and Clifty Falls State Park. 🚙 On street parking only. The space This two bedroom home includes a comfortable living room. There is a TV with a Roku and board games for your entertainment. There are two bedrooms and one bathroom. Both bedrooms feature a ROKU TV, king sized bed with memory foam mattresses, and storage space for your things. An extra set of towels will be found in the closet should you need it. A desk and office chair is found in the hallway for your use. High speed internet is available as well. A Google Nest thermostat is used in this home. The full kitchen provides a variety of kitchen supplies. A washer and dryer is available for your use. Please remember to bring your preferred detergent. A starter supply of paper products such as paper towels and toilet paper will be provided. Outside, you will find a cozy porch as well as a side yard to enjoy. Guest access Guests will have full access to the home, porch, and yard. Street parking only. Other things to note This historic home has been renovated but the flooring is slightly uneven in some areas, including doorways, so please watch your step. There are four security cameras on the outside of the home. This home accommodates up to four adults. Up to two well-behaved dogs (35 pounds or less) with payment of the pet fee. Please crate dogs whenever they are left unattended, clean up pet waste from the yard, and wipe dirty paws before coming inside. A couch cover is provided for pets and is usually in place before arrival. For last-minute bookings, you may need to place the cover on the couch upon your arrival. Please read the cancellation policy carefully before booking. This is the policy that will be followed if a cancellation occurs.

1 Block to Main St~2 King Beds~Downtown Cottage!

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. The space You will have access to all pictured spaces. There are 13 steps to the second floor where bedrooms and bathroom are located. The finished attic is our private space and off limits to guests, but will never be occupied during your stay. Guest access Access to the basement washer and dryer is available upon request. There are 13 steps to the second floor where bedrooms and bathroom are located. Other things to note This old home has 4 steps at the entrance and 13 additional steps to the second floor bedrooms and one bath. We welcome all but do not recommend our home for guests with mobility issues. Street parking only. The space in front of the home is almost always available. If not, you may unload in the alley next to the home and find a street space nearby. Pack and play, baby monitors and noise machine available. We are located by a fire station but have gone weeks at a time without hearing a truck.

Cozy downtown home with patio. Walk to everything.

Spacious & stylish period home furnished like you’re traveling back in time - or escaping it. With an eclectic mix of decor from antique federalist style to fun MCM, the owners designed it to feel like a cozy library. Ready to see historic Madison? Walk 3 mins to Main St where you’ll find the Attic, Mad Love, Trolley Barn, & Olde Tyme. On Saturday mornings, take a 7-min stroll through Madison’s most stately brick homes down Third through Mill, Vine, Elm, and Broadway to the Farmer’s Market. The space We want you to be as comfortable as possible in our newly restored space (aka The Garden Home in our Book Haven collection!). Please note: The layout is four rooms back-to-back in a shotgun style with a door separating each of the two bedrooms. There’s beautiful and comfy bedding for four (two separate rooms with queen beds), towels, pillows, built-in cabinets, and dressers, and many options for stashing your stuff. The bathroom and kitchen are at the back just beyond the second bedroom, and the kitchen is well equipped with everything you need if you choose to eat in. Enjoy a full-size fridge, full electric oven, microwave, coffee maker, toaster, and full dishware set. There's also a washer and a dryer if you need to do laundry. Beyond the diner booth & chairs for two, there’s a covered outdoor table with seating for four overlooking our beautiful English garden. A 55-inch Samsung TV with free Roku/YouTubeTV and fast 300Mbps Wifi is located in the living room at the front of the house. This is truly a home away from home. Guest access You have the entire house to yourself. Other things to note The owners live just 5 minutes away and keep part of their extensive book collection in Book Haven. We ask all guests to take good care of our books! Self check-in is through a keypad. NOTE: This is a shotgun-style house with all four rooms back to back, so you have to walk through the 2nd bedroom to reach the kitchen & bathroom at the back of the house (although there is a door separating the two bedrooms). Also, the house isn't perfect for little kids as there are lots of little breakable items & trinkets. Although fine if a beyond toddler stage :) All pictures you see are within a beautiful 3-7 minute walk!

The Garden Home by Book Haven - Steps from Main

Newly renovated shot gun house, great location in downtown Madison Indiana. Only one block from Main Street where there is shopping and restaurants, and four blocks from the river front. Two bedrooms each with a queen size bed, one bath, fully stocked kitchen, small private backyard. Washer and dryer on site, on street parking.This property is a shotgun style home which means you walk through one bedroom to get to the next, but there is a door between.

Lavender House

Take it easy at this unique and tranquil getaway.A unique 150 yearls old Historical house on Main Street! SINGLE STORY !!This house is only few blocks away from downtown river walk. This property has a unique history and a very unique layout. It has almost a wrap-around front porch, and has ample character in its side and rear yards. Great lighting exists here, and the white shines throughout the indoors and outdoors. Other things to note we have total of five beds. one queen , two fulls and two twins. The two twins are trundle beds. You have to move beds aside to use both trundles. We can make that ready if we were informed in advance

Beautiful Bungalow on Main

Did you ever wish your decor showed your quirky side? That’s what we’ve done. If Pottery Barn theme is your vibe you will be disappointed BUT if your adventurous side likes eclectic,boho meets MCM space that’s not perfect but perfectly imperfect, this is for you. 3.5 blocks to the tourist area and 4 blocks from the river. Quiet street and pet friendly. We also have a licensed, insurance and tagged 4 person golf cart for rent if interested. Madison is a huge golf cart city. The space Living room eat in kitchen 2 bedrooms with queen beds 1 bathroom with shower 1 bathroom with tub 2nd living room with futon with easy access to the porch Outside space with fenced in yard ( dog friendly) 1 off street parking space however most people choose to park in the street in front of the house. There is always available parking. Laundry room with washer dryer Guest access All spaces except garage and owner’s closets Other things to note We are constantly improving our space. It will always be a work in progress. So if the towels don’t match the current bathroom decor it will EVENTUALLY! Remember our Airbnb was once our home and we always want it to remain a home for family, friends and now welcomed guests. Side note we also own The Red Bicycle Hall music venue! If there is a show when you here you’d like to see I bet we can give you an Airbnb rate. 😉

Fiona’s Boho  Retreat

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.

Charming shotgun in the heart of downtown Madison

Welcome to our cozy, character-filled home in the heart of historic downtown Madison! Built in 1850’s, this shotgun-style home is just steps from local restaurants, antique shops, and the scenic Ohio Riverfront. Whether you're here to explore the charming streets of Madison, Clifty Falls or simply relax, this home is the perfect spot. If you love history, charm, and a little bit of quirk, you’ll feel right at home. Book today and experience Madison in a space that’s as unique as the town itself! The space Step Inside – A Shotgun-Style Adventure! Our home follows a classic shotgun-style layout, meaning you’ll walk through each room in a straight line—like a fun little journey through time! Here’s what to expect: 🍽️ Fully Equipped Kitchen – Whether you’re cooking up a meal or just grabbing a morning coffee, this kitchen has everything you need. Yes, the floors have a little personality (hello, history!), but that just adds to the charm! 🛁 1 Full Bathroom – Conveniently located, stocked with essentials, and ready to help you refresh after a day of exploring. 🛏️ 2 Cozy Bedrooms – 🌙 Bedroom 1: Features a comfy queen-sized bed, perfect for stretching out after a long day. ⭐ Bedroom 2: Offers a snug full-sized bed, great for curling up with a good book or a restful night’s sleep. 🔥 Cozy Living Area – Unwind by the fireplace, stream your favorite show, or just soak in the historic vibes. 🌿 Private Backyard & Charming Front Porch – Whether you prefer morning coffee while people-watching on Main Street or a quiet retreat in the backyard, this home gives you the best of both worlds. What Makes This Home Special? 🏡 Historic & Full of Character – Built over a century ago, this home has stories to tell! Expect charming quirks like slightly uneven floors, adding to its vintage appeal. 📍 Perfectly Located – Walk to the best local spots or enjoy a short drive to Hanover or Louisville. ☕ Front Porch Vibes – Sip your coffee and watch the world go by on Main Street! Other things to note With Old Homes Come Quirks – and That’s Part of the Fun! Like any house that’s been standing for over a century, this home has a personality all its own. No matter how hard we try, some things just won’t change—like the hallway floors, which have decided they prefer life a little uneven. It’s all part of the charm, and we think it adds to the story of this historic gem. If you appreciate homes with history and character, you’ll feel right at home here!

Historical Shot Gun Home On Beautiful Main Street

This fully furnished 2-story home was built in 1900 & retains the era's charm, yet has modern conveniences - indoor plumbing & central A/C! It easily sleeps 6 people and is ready to go - just bring your toothbrush :-) The space The home has 2 bedrooms (1 king, 1 full) upstairs, plus a sofa bed on the main level, 2 full baths, a fully-equipped kitchen, dining room, W/D, 2 gas fireplaces (1 in master bedroom), 3 flat-screen TVs with Netflix & Pandora (plus basic cable in living room), WiFi, wrap-around front porch with swing & rocking chair, deck with outdoor furniture, and gas grill. The front yard is enclosed with the original wrought-iron fence. If you're in the area for an event in Louisville (e.g, the Derby!) or Cincinnati, you'll be within an hour's drive and will have a relaxing home to return to each evening. Guest access Guests will have access to the entire house and yard for the duration of their stay.

Historic Home on Main St., USA

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. The space In 1860, this space was the hayloft to a livery stable. Look at it now! The new construction and furnishings have created an upscale luxury apartment you will love! It will be a memorable stay... and you can share many photos w your friends, if desired. Guest access There are 2+ bedrooms 2 luxury bathrooms new laundry room gourmet kitchen living room dining room office spacious gathering area. Other things to note This is a loft area so there is a fully lighted stairway (newly constructed) leading to it with sturdy railings. * pets are not permitted * no smoking or open flames (or candles) * no parties keypads for guest entry

Livery Loft: BEST location!

Modern flair with antique charm sets this BnB apart! Located on quiet street in the heart of historic downtown Madison, this fully renovated 1830s Row House has you steps away from everything! Whether it's a festival or fall colors, a boat race or car show on the riverfront, a micro brewery or winery, antiquing or historic tour, hiking Clifty Falls or simply just getting away, we have the location for you. *HVAC system includes whole-house air purifier. Max of 4 guests, no children under age 8. The space From the morning light flooding through the front windows to welcome the day, to the fire bowl in the private courtyard in the back to bring it to a close, this historic home with modern flair provides everything you need to create wonderful memories each day of your stay. The restored, original hardwood floors make it feel like you are walking on history. Curl up on the couch in the living room with a book and enjoy the replicated coal-burning fireplace. A fully equipped kitchen (including Keurig, coffee, tea, water) and washer/dryer unit add all the conveniences of home. *For your safety, a whole-house air purifier that kills 99% of viruses, has been installed with the new modern HVAC system controlled by Ecobee. The calendar only opens up dates three months in advance. If you are interested in booking further our, message owner to check availability and special pricing. Guest access Entire home and back courtyard Other things to note Early check-in or late check-out is usually available. Just include your request when making your reservation and I will try to accommodate whenever I can. Staying seven nights or more will include a 20% nightly discount.

The Row House

Beautiful historic 1830s log cabin nestled in the woods of Dugan Hollow! A 2-story cabin with 2 authentic lofted bedrooms, an indoor jacuzzi tub, fireplace and baby grand piano. Uniquely situated only 5 minutes from Historic Madison, Indiana on the Ohio River; 15 minutes from Clifty Falls State Park; and 20 minutes from Big Oaks National Wildlife Refuge. *Small dogs allowed with prior approval, see below.* The space The Cabin sleeps up to 6 guests. It has 2 lofted bedrooms - one with a King and another with 2 Queen beds. There is an oversized Jacuzzi tub for two in the bathroom, and a wood- burning fireplace and baby grand piano in the great room. The Cabin's decor is Americana throughout with unique, regional historic pieces including antique quilts from the late 1800s. The spacious kitchen is equipped to prepare home-cooked meals for 6. For outdoor cooking, there is a propane grill, a charcoal grill, and a fire pit! Additionally, The Cabin has an oversized deck with beautiful views of Dugan Hollow and a seasonal waterfall. The Cabin is not recommended for children younger than 8 years old due to open railings on the lofts and the deck. Guest access Guests have access to the whole Cabin, including the porch, deck and parking areas. Other things to note The Cabin is historic. Some of its charm and features do not comply with modern standards. For example, the stairs in the Cabin are irregularly shaped and may be challenging for guests with mobility issues. Guests may be accompanied by one (1) small, house-trained dog with prior approval. The dog should be kept off beds and furniture and should be crated if left alone. Multiple dogs, large dogs, or other pets are not permitted.

Historic 1830s Log Cabin in Madison, IN

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 and Clifty Park. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. The space This is a cozy cottage with a full kitchen, coffee bar and nice relaxing porch surrounded by nature and trails to explore. There is extra parking below. Pets are allowed with permission and extra fee of 50$. There is a dog door and small area in the back for the pet. There is a fire pit outside. Please follow listed rules. Guest access Coded entry. Other things to note Fire pit. Please make sure to use with full supervision. It is not allowed to be used by children. Please make sure gas is turned off after use. Please never leave any child unattended by it. Please remember to close the lid after use. Please do not move it to a different location.

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Experience the charm of a New Orleans style shotgun house at Carpet Alley in the heart of historic downtown Madison, IN. Offering all the amenities of home, our centrally located getaway is perfect for exploring local antique shops and admiring the stunning Ohio River. Whether you're looking for a romantic weekend, or time to yourself, our inviting home is the perfect retreat for your next getaway. Other things to note The home is located in the heart of downtown. As with any downtown location, guests can expect typical downtown activity, including vehicles on the street and people enjoying the charm and energy of beautiful downtown Madison!

Carpet Alley

Nestled in the heart of historic Madison, Indiana, this nineteenth-century home has stood proudly at the corner of Fifth and Mulberry Streets for more than 150 years. Where others saw a crumbling house, we saw potential. Through a true labor of love, this historic gem was thoughtfully restored, honoring its original character while breathing new life into every corner. The home blends timeless architecture with modern comfort, an inviting space full of history, warmth, and renewed beauty. The space Welcome to American Mulberry – A Thoughtfully Restored 1850s Gem in Historic Madison, Indiana Step into history and comfort at this beautifully restored circa-1850 home, located in the heart of Madison—a vibrant town known for its festivals, art events, parades, and charming Main Street, all just a short walk away. This elegant residence perfectly blends historic charm with modern luxury. The home features: -Two spacious master suites with private full bathrooms -A half bath for added convenience -King and Queen beds with room-darkening automated blinds -Beautifully tiled showers for a touch of spa-like luxury -A comfortable living room with a full-size sleeper sofa -Unwind on one of the two outdoor decks—perfect for morning coffee, reading, or simply enjoying the peaceful surroundings. Head downstairs to the recreational basement featuring a ping pong table & foosball—great for family fun or a friendly challenge. The home's kitchen is a chef’s dream, outfitted with premium ZLINE appliances and stylish finishes, ideal for cooking or entertaining. Outside, admire the reverse stencil American flag mural and custom metalwork that reflect the care and craftsmanship of the restoration. Located in a golf cart- and bike-friendly neighborhood (rentals available nearby), this home offers a prime location just minutes from the heart of Madison’s historic downtown. Why You’ll Love It: ✔ Historic charm with luxury upgrades ✔ Walk to festivals, shops, and the riverfront ✔ Perfect for couples, families, or a friends’ getaway ✔ Comfortably sleeps 6 with flexible sleeping arrangements ✔ Unique design touches inside and out Book your stay at American Mulberry and experience the best of Madison—where history, hospitality, and charm come together. Guest access You have access to the entire house, except 1 locked owners area. Home Layout: Main Level -kitchen -living room w/sleeper sofa -half bathroom -back deck with seating Upstairs -king master bedroom w/full bath & deck with seating -queen master bedroom w/full bath -laundry closet Downstairs -ping pong table -foosball -games Additionally, at the rear of the home, the garage and the apartment located above it are not accessible to guests and may be occupied during your stay. The apartment has a completely separate entrance and does not share any interior space with the home; only the driveway is shared. We kindly ask that you refrain from blocking the garage doors during your stay. This area is reserved as the owner’s private space. Other things to note -This listing is for the home only. -This listing has a shared driveway with the studio apartment over the garage. -This listing does not have garage access. -This listing is not suitable for children or pets. -You must be able to climb stairs to access the bedrooms and laundry room on the 2nd floor. -You must be able to go down a stairway to the basement to get to the ping pong table.

Luxury Historic Stay K/Q Suites, Sleep Sofa, Decks

River's Edge II-Historic Hunger House-Downstairs

Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride, from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park. The space Our two-story home features two inviting bedrooms upstairs, each offering captivating views of the Ohio River. The master bedroom boasts a plush Queen bed, while the second bedroom features a cozy Full bed. Both bedrooms share access to a full bathroom, ensuring comfort and convenience for all guests. Downstairs offers a comfortable memory foam queen sleeper sofa for additional sleeping arrangements. A second full bathroom is conveniently located on the ground floor, providing added flexibility and privacy for guests. Our home can comfortably accommodate up to 6 guests. Step outside onto our expansive deck, that can be used for extra entertaining space with two separate sitting areas where you can bask in the tranquility of the surrounding forest while sipping morning coffee or enjoying a sunset dinner. Inside, a fully equipped kitchen awaits, complete with a versatile Keurig machine catering to both k-cups and ground coffee enthusiasts. Other amenities include a washer/dryer, three Smart TVs, complimentary high-speed Wi-Fi, a hairdryer, and onsite parking for two small/medium size vehicles in most cases. Guest access The entire house is accessible, with the exception of: mechanical room/storage closet in downstairs bathroom, lower pantry cabinet to right of refrigerator, and our wifi/communications cabinet above microwave.

Glenda’s Overlook

We welcome you to come enjoy all the charm downtown Madison has to offer! This early 1900’s home has been newly updated, while still keeping its cozy, historic feel. It is located a walkable 3 blocks from Main Street and just a couple blocks further you will find Madison’s beautiful waterfront view of the Ohio River. Come fall in love with the famous Madison, IN and all there is to experience! The space When you enter this home you will find the inviting living room featuring comfortable seating, a large smart tv, and some games for an entertaining night in! The couch converts to a futon bed with provided bedding if needed. There are two spacious bedrooms. Bedroom 1 features a comfortable Queen size bed, dresser and hanging rack. Bedroom 2 houses a comfortable King size bed, dresser and hanging rack. This bedroom also has a full bathroom attached (toilet, vanity and walk-in shower). You will love this home’s bright, open, clean kitchen. It features an island with 4 barstools for dining, stainless steel appliances, a large drop-in sink and a coffee bar we take pride in keeping well-stocked for our fellow coffee lovers. Kitchen is equipped with everything you will need for cooking such as pots, pans, utensils, oils, mixing bowls and seasonings. You will find an additional full bathroom off the kitchen with shower, toilet, vanity and full-size washer and dryer. You will notice the beautiful 10’ ceilings in every room giving the home that open, airy feel. All living space is located on one floor. The entire home has free WiFi. There is no cable, however, the SmartTV allows you to log into all your streaming apps such as Netflix, YoutubeTV, Hulu, etc. The front entry way is a beautiful, cozy spot to un-plug and unwind with your morning coffee or evening beverage. Other things to note Check in time is 3pm, check out time is 11am. On Street Parking Only, you will likely be able to park right in front of the house. We will provide a "starter supply" of paper towels, dish detergent, trash bags, toiletries, etc.

Walk to Main St- Cozy Beds/Clean!

Full time Airbnb 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 The space Back yard joins with Legacy Park and has an amazing Ohio River View. Our house is 1 Block from Bicentennial Park! Historic Madison, Indiana, has been crowned the #1 Small Town in the Midwest by the esteemed USA Today 10Best Readers' Choice Awards. After a rigorous selection process involving a panel of esteemed experts and four weeks of intense public voting, Madison emerged victorious, solidifying its status as a top destination in the heart of the Midwest. "We are overjoyed and deeply honored to be recognized as the best small town in the Midwest by the USA Today 10Best Readers' Choice Awards," said Andrew Forrester, Executive Tourism Director for Madison. "This accolade is particularly special because it's voted on by the people, showcasing our destination as one that is truly loved by visitors and residents alike." In addition to the support of the community and visitors, Forrester also extended gratitude to the marketing team for their dedication in keeping Madison's nomination top of mind throughout the voting period. "With strategic marketing efforts and the passionate engagement of our residents and visitors, we were able to showcase the unparalleled beauty and charm of Madison to voters across the country," Forrester added. Madison's charm extends beyond its recognition as the #1 Small Town in the Midwest. As the largest contiguous National Historic Landmark District in the US and an Indiana Cultural District, Madison continues to garner attention for its rich history and vibrant culture. Additionally, being named a 2024 Semi-finalist in Main Street America’s Great American Main Street Award further solidifies Madison's status as a prominent destination in the Midwest. "We extend our heartfelt gratitude to everyone who cast their votes and helped secure this prestigious accolade for our beloved river town," said Mayor Bob Courtney. "Your support is truly appreciated and serves as a testament to the special bond shared between our residents and visitors, and the dedication of our community.” "This honor highlights the extraordinary experiences our town offers to visitors, from our historic architecture to our vibrant arts & music scene; now the rest of America can experience what we get to enjoy every day!" Mayor Courtney added. "It's also worth noting that our neighboring city, Vevay, Indiana, was the Best10 winner last year. This camaraderie between neighboring historic small towns highlights the unique charm and appeal of our region." With its well-preserved 19th-century architecture, thriving arts & music scene, and scenic location along the Ohio River, Madison offers a one-of-a-kind experience for travelers seeking history, culture, and natural beauty. Guest access access to the entire house except locked cabinets

Riverview Historical Retreat

Walk Across Ohio River | Perks for Pups | Golf Cart | Coffee & Tea Station Historic sights, good eats, and outdoor fun on the Ohio River await when you stay at this 2-bedroom, 1.5-bath vacation rental in historic Madison, designated as one of the best small cities in America. The cozy bungalow comes with everyday essentials, including a full kitchen, dedicated workspace, and fenced yard for fur babies. Ready to explore? Madison has 133 blocks of local shops, cafes, restaurants, and more! The space SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa  INDOOR LIVING - 3 Smart TVs, DVD players, DVDs - Board games, puzzles, books, CD player, CDs - Electric fireplace - Dining table - Work desk (bedroom 1) - Portable desk  OUTDOOR LIVING - Covered back patio, outdoor dining set - Fenced-in yard (15'x40') - Front porch w/ 2 chairs - Golf cart (waiver required)  KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Keurig coffee maker, coffee & tea, flavored syrups, cream & sugar, mugs & to-go cups - Spices, toaster, blender, Crockpot, air fryer - Cooking & baking basics, dishware & flatware, trash bags & paper towels  GENERAL - Central A/C, gas heating - Towels & linens, complimentary toiletries, hair dryer, lap blankets - Washer & dryer, iron & board, hangers - One-medium sized dog crate, dog dishes, pet throw blankets, waste bags, welcome treat - Free WiFi, keyless entry  FAQ - 3 exterior security cameras (facing out) - Pet fee (paid pre-trip)  ACCESSIBILITY - Single-story home, 3 steps down to walkway + 1 additional step to enter - 1 interior step to access primary bedroom, bathroom & laundry room - Uneven flooring in entryway  PARKING - Driveway (2 vehicles, behind property) - Free street parking - Free public parking throughout the city Guest access Guests will have access to the entire property via keyless entry Other things to note - No smoking or vaping - Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 2 pets max) - Please crate dogs when left alone at the house. One medium-sized crate will be provided - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - The main point of entry is a side entrance which may be accessed from the front or rear of the property - The designated parking spaces are located at the rear of the property. There are 3 steps down to the paved walkway leading to the side entrance of the house. There is 1 step down halfway to the door on the sidewalk. There is a ramp (leading past the golf cart) that may be used to avoid the 4 steps, but you will walk through large gravel in the yard - There is 1 interior step required to reach the primary bedroom, full bathroom, and laundry room. Inside the main entry, there is a cellar door covered by a rug that may cause guests to feel a slight give in the flooring, which is normal for the house - A waiver is required prior to using the golf cart - Please note that the full bathroom can only be accessed through bedroom 1 - Your safety matters. This property features 3 exterior security cameras. Camera 1 is on the front door facing the street. Camera 2 is a doorbell camera on the main door facing the exterior entry. Camera 3 is on the back corner of the house facing the parking pad. The cameras are outward facing and do not look into interior spaces. The cameras record video when activated by motion

East End River Retreat: Dogs Welcome!

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”. The space This apartment is not a shared space but is for your exclusive use while staying. The 2 comfortable bedrooms and 2 spacious baths offer luxury linens and bath products. There is an adjacent separate area in the entrance foyer with the second restroom and laundry area that you may also use. It’s a great space to unload your car and store your extra things. This outer hallway may be occasionally used by me or my husband if we are working in the garage area but it is separate from the apartment (just outside your French doors). I will advise you if we need to come into that area (although it is very seldom.) Guest access The entire private apt is yours to enjoy. You will be given a keypad code before you arrive so you can check in easily. Other things to note This historic building originally was the city stable in circa 1886. It’s now a blend of barnwood contemporary and vintage charm And, just as other guests, you will love our best downtown ! We’re steps away from the river, all the festivals, the music, coffee shops, eateries,and shopping, all right around the corner on Main street ! New renovations, spacious rooms, many TVs and comfortable furnishings will leave you wanting to stay longer. Some see why both of our apts (also Livery Loft) were awarded “Best Places to Stay in Madison! Also see our guidebook to see all that we provide to make your trip/stay more fun!

Stablemaster’s Quarters/
Best downtown location!

Get away from the city life and come stay down at Riverside Camp and Ramp. This camper is nested on a beautiful view of the Ohio River just 3 miles outside of Madison, IN. Get away from it all when you stay under the stars at the Riverside O-Asis! Early check in is available for $25. Reach out for early check in needs. Message me directly on the messaging thread. The space The main bedroom has a queen short bed. The bunks are full over full. The table and couch also make beds.

Riverside O-Asis

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, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill The space You'll be greeted by an impressive, spacious great room flooded with natural light from soaring windows met with a vaulted ceiling and exposed timbers. This newly updated home, along with fresh furnishings, was carefully curated to inspire comfort. The rich tones in the new floor contrast the white walls in the large adjacent bedrooms to strike a perfect balance. This beautiful, mid-century home, which was designed and built by my grandparents, offers a fully equipped kitchen including coffee, creamer, bottled water and assorted soft drinks. Upon entering the house there are seven steps to go down to the main floor. Everything is on the main floor of the house. The washer and dryer are available for you to use. Parking is available on our paved driveway. Relax with a cup of coffee or a glass of wine or barbeque on the gas grill on the backyard patio. Enjoy your stay at the Artist's A Frame. 4 Guests | 1 King Bed | 1 Queen Bed | 1 Bathroom Guest access The entire home is accessible to guests except the the garage and upstairs area which is unfurnished and never occupied. Upon entering the house there are seven steps to go down to the main floor. Other things to note You may see wildlife on the property including deer and squirrels.

The Artist’s A-Frame

Peaceful Retreat or Heart of the Activity There is easy access to all things Madison from this beautifully updated, well furnished, centrally located home Only 2 blocks to Main St shops, dining & festivals Just feet from the Ohio River puts you on the doorstep of the Riverwalk & all festivals on Vaughn Dr Unobstructed, breathtaking views of the Ohio River & Madison Bridge Just 200 ft to public boat ramp & street parking spacious enough for a boat makes this a boaters dream This home has it all! The space 2 bedroom, 2 bath single story home Other things to note There are security cameras on the exterior of the property. These cameras only view the property entrance/exit points, such as doors and gates.

River Living - Beautiful Views of the River

Lucky Shamrock is an absolutely charming historic cottage centrally located in Madison. Not only is the cottage cute beyond belief, but you also get the pleasure of HOG HEAVEN for outdoor dining and get togethers. The space Each bedroom has a queen bed and a full bath and a private entrance from outside . We have it set up as a 2 bedroom for short term. If you had an interest in a longer term rental we can change the front bedroom into an additional living space. Plenty of parking . Lots of yard space. Only 1 and 1/2 block to Jefferson st where all the action starts. I block south and you are on Madison’s amazing riverfront walk. Original claw foot bath tub in this 120 yr old home. Central heat and air along with WiFi blend the comfort of new with the charm of old.

Lucky Shamrock

Ask about monthly discount! Come enjoy all downtown Madison has to offer! This early 1900’s home has been completely updated to give a fun, modern feel. It is located a walkable 3 blocks from Main Street and just a couple blocks further you will find Madison’s beautiful waterfront view of the Ohio River. Very close to Kings Daughters Health Hospital and other healthcare facilities, as well as industrial construction sites and Hanover College. You will feel right at home here during your visit The space When you enter this home you will find the inviting living room featuring comfortable seating, a large smart tv, and some games for an entertaining night in! There are two spacious bedrooms- Both bedrooms feature a comfortable King size bed, dresser and hanging rack. There are 2 full bathrooms in the home which each feature their own shower, vanity and toilet. The kitchen flows openly from the living room and features an island with 4 barstools for dining, stainless steel appliances, a large drop-in sink and a coffee bar we take pride in keeping well-stocked for our fellow coffee lovers. The kitchen is equipped with everything you will need for cooking such as pots, pans, utensils, oils, mixing bowls and seasonings. Feel free to utilize the home's full-size washer and dryer during your stay! All living space is located on one floor. The entire home has free WiFi. There is no cable, however, the SmartTV allows you to log into all your streaming apps such as Netflix, YoutubeTV, Hulu, etc. The covered patio is a cozy outdoor spot with string lighting. The perfect spot to un-plug and unwind with your morning coffee or evening beverage. Other things to note *Please note the front bedroom is nearest to the main road and you may hear noise as cars drive by. We provide a sound machine and ear plugs for our sensitive sleepers* Check in time is 3pm, check out time is 11am. On Street Parking is available on the side-street of the house. You will likely be able to park on the street area closest to the front of the house. We will provide a "starter supply" of paper towels, dish detergent, trash bags, toiletries, etc.

Long or Short stay-King beds

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.

Warren’s Guest Cottage

Annies Fabulous Federal house

Madison Manor II is a welcoming historic townhouse designed for making memories. With vintage charm, modern comforts, & room for 8—including your dog—it's perfect for family getaways or friend groups. Traveling with a larger group? Book adjoining Madison Manor I too. Walk to the river, enjoy downtown Madison, or explore Clifty Falls Park. Then unwind on the shared patio with a hot tub, fire pit, and grill, play a game of darts, or gather around the "big screen" for family movie night. The space Welcome to Madison Manor II, a beautifully restored historic townhouse in the heart of downtown Madison, Indiana — just steps from the Ohio River, shops, restaurants, wineries, and scenic walking paths. Madison Manor II adjoins Madison Manor I. Each townhouse has its own private entrance, bedrooms, living room, kitchen, and game room. You may hear guests from the neighboring unit; earplugs and white noise machines are provided for your comfort. — Highlights — • 2-story Townhouse • Private entry • See layout photo • 2 bedrooms • 2.5 bathrooms • Sleeps 8 — 6 guests + 2 small children • 2 Queens · 2 Twin futons in game room (common area) · Toddler mattress · Pack-n-Play • Ideal for families, groups, and couples • Walk to Downtown Madison & the Ohio River • Free street parking • Fully equipped kitchen • Ultra-fast WiFi • 3 Smart TVs • Washer & dryer in shared laundry room • Patio • Hot tub • Fire pit • Gas grill (shared amenities) • Dedicated game room • Mini movie theater • Dartboard • Poker set • Board games • Golf cart rental (subject to availability) • Adjoins Madison Manor I — book both townhouses & sleep up to 16 • Quiet, well-mannered dogs welcome with prior consent • Pet fee applies — The Details — This Italianate-style townhouse built in 1870 offers a rare combination of prime location, architectural character, and standout amenities. Whether you’re visiting for a weekend getaway, a family trip, or an extended stay, Madison Manor II is designed for relaxation, connection, and memorable experiences. Inside, historic charm meets modern comfort with exposed brick and thoughtful décor. The well-equipped kitchen includes pantry basics and everything you need for easy meals at home. Curated spaces throughout the home invite you to unwind after a day of exploring. Spend evenings soaking in the hot tub beneath pergola café lights, gathering around the fire pit, or enjoying movies, games, and friendly competition indoors. The home is pet-friendly, making it easy to include your four-legged companion on riverside strolls or hikes at nearby Clifty Falls. Thorough cleaning protocols between guests ensure a spotless and sparkling stay. Sleeping arrangements (sleeps 6 comfortably + up to 2 infants): • Primary bedroom (2nd floor): Queen four-poster bed with ivory bedspread, vintage charm, TV, and storage • Second bedroom (2nd floor): Queen bed with calming natural light, TV, and storage • Full bathroom (2nd floor): Located steps from both bedrooms • Living Room 2 / Game Room (1st floor): Two twin futons • Second full bathroom (1st floor): Walk-in shower • Pack ’n Play and toddler mattress provided Step outside to a shared backyard oasis featuring: • Pergola with café lighting • Hot tub for year-round relaxation (closed below 20°F) • Fire pit for cozy evenings • Gas grill and outdoor dining area 📍 Unbeatable Location • 10-minute walk to downtown Madison • 2-minute walk to the Ohio River • 5 blocks to boat ramp — wide on-street 1 block away for trailer • 10-minute walk to Milton–Madison Bridge walking path • 10-minute drive to Clifty Falls State Park • 15-minute drive to Hanover College • 10-minute drive to Madison Hilltop You’ll be close to everything — yet tucked on a quiet residential street in the heart of Madison, the largest contiguous historic district in the U.S. — Why We’re Different — • Hot tub — a rare amenity in Madison • Dedicated game room with mini movie theater — also rare • Walk-to-everything convenience reduces event-day parking chaos • Convenient onsite golf cart rental (subject to availability) • Historic charm paired with modern comfort upgrades • Excellent for Regatta, Chautauqua, Hanover College visits, and festivals • Complimentary chocolate, snacks, and chilled sparkling water • Room darkening curtains, ear plugs, & Dohm machine for restful sleep 👶 🧒 Family-Friendly Features • Highchair • Baby bath • Pack ’n Play • Toddler mattress • Game room with mini movie theater, dartboard, poker set, board games, and cards • Bathtub in upstairs bathroom • Quiet neighborhood ideal for evening walks ✨ Outdoor Living • Patio with pergola and café lighting • Hot tub and fire pit for shared outdoor relaxation • Gas grill with grilling tools • Outdoor tables and seating for group meals or downtime 🐾 Pet-Friendly Perks • Medium crate and dog bed • Food and water bowls • Waste bags conveniently provided near the front door • Patio tether • Sofa cover 🌱 Sustainability — Lower Your Travel Footprint • Local coffee ☕ with reusable filters • Fresh, local flowers (in season) • Recycling provided • Refillable dispensers with shampoo, conditioner, and body wash • Eco-friendly toiletries like bamboo toothbrushes • Eco-friendly cleaning products + “free & clear” detergent • WiFi-enabled thermostat 🏡 House Rules Quiet hours: 10pm–8am (City of Madison ordinance) No parties or unauthorized events Only registered guests permitted overnight Dogs allowed with prior approval and pet fee No smoking or vaping anywhere on the property Please remove shoes indoors Check-out: simple list provided in home Hot tub rules posted onsite Pet rules: (1) Must use sofa cover provided; (2) Pets not permitted on any other furniture (3) Leash required on the patio. Guest access All parts of the home are available to guests. There is a shared laundry room and patio, hot tub, fire pit, and grill.

"Madison Manor II” •Hot Tub •Walk to the River

Escape to our charming 2-bedroom house, nestled along the serene banks of the river in Milton, KY. Whether you're looking to unwind or explore, this cozy home offers the perfect balance of comfort and nature's beauty. Best of all, you're just a 2-minute drive or a scenic 25-minute walk from the historic and charming downtown Madison, Indiana. Explore local shops, dine at unique restaurants, or stroll along the riverfront. The space 2 spacious bedrooms, each with its own full bathroom. The center of the home features a large open floor plan with expansive windows that provide beautiful views of the Ohio River. The kitchen, living room, dining room, and a convenient half bath are all located in this central gathering space. A wet bar is set up for guests next to the door leading to a 40-foot covered porch overlooking the river, the Milton-Madison Bridge, and historic downtown Madison, Indiana. The home’s entryway is located on the lower level, where you’ll also find the washer and dryer. From there, you’ll walk up approximately 13 steps to reach the main living area. Please note: The home is located next to a well-traveled road, so some traffic noise should be expected. For your comfort, sound machines are provided in each bedroom if you’d like to use them while sleeping. Directly in front of the home is the Milton Boat Ramp, which can occasionally become lively, especially on weekends and during nice weather, with increased activity from boaters and visitors.

The Porch at Milton

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.

The Atlas

Welcome to Eleonora's Cottage, the cutest Air Bnb in Madison. Circa 1899, you will love the wraparound porch, the cozy bedrooms, a full size living room, kitchen and the cute bath. Eleonora's Cottage is perfect for parties consisting of 6 or fewer guests, with 3 bedrooms, new mattresses and lovely bedding. Located on Main Street, within walking distance of the Heritage Trail, local restaurants and downtown shopping. We also have off-street parking and a fairly large yard. The space Outdoor seating on the wraparound porch 9 months out of the year, perfect for reading, enjoying a glass of wine or dining al fresco. Also for relaxing after a busy day of shopping.

Eleonora's Cottage On Main

Keep it simple at this peaceful and centrally-located place. This historic home offers three comfortable bedrooms and a tons of outdoor seating. Enjoy all that Madison has to offer - live music, historic landmarks, specialty shops, the beautiful riverfront, and amazing festivals, all within a short walking distance, a trolley ride, or a short car ride. The space Historic 3 bedroom, within walking distance of Main St. downtown Guest access The entire home is included with your rental. Other things to note All bedrooms are located on the second floor. Off street parking is available, primarily for compact cars.

East Street Retreat

Located in the Madison Historic District, you will be close to everything when you stay at our centrally-located home. We are located just two blocks north of bustling Madison Main Street, a perfect place to stay with family or friends. The space The home includes all that you need for a relaxing (or busy!) trip to Madison. The main level contains the living, dining, and laundry rooms, along with a full bath, kitchen and master bedroom. Two bedrooms with a shared a half bath are located on the 2nd floor. Bed linens, towels, extra blankets and pillows, and other necessities are provided. The kitchen is fully equipped if you decide to stay in for a quiet night instead of trying one of Madison's great restaurants. Guest access Guests will have access to the entire home. Other things to note This historic home has central heating and air conditioning on both levels, controlled separately. NOTE: Maximum number of guests is 6.

Cozy 3 bedroom home, steps away from Main Street

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. The space Located just outside city limits of Milton, Ky. 1 mile from Downtown Madison, 3 miles from the South entrance of Clifty Falls State park and 2 miles from Richwood on the River. Lots of outdoor space overlooking the banks of the Ohio River. Plenty of room for outdoor games and fishing. Large deck and outdoor pavilion great for relaxing and watching the riverboats, stunning sunsets and views of historic downtown Madison, IN. Guest access Please don’t encroach on neighboring property. Life preservers are NOT available and it is NOT recommended to swim in the river. Guests have full access to the outdoor pavilion , firepit and grill. Paper supplies and refrigerator items in the pavilion are not for guest use. Other things to note 2 bedrooms, one with queen bed the other with 2 twin beds that can easily be joined to make a king. There is a small loft accessible by ladder with queen air mattress. Porch sofa folds to twin. Has all common house hold amenities (dishes, utensils, pots/pans, microwave, toaster, blender). Coffee maker is a K-cup type.

Milton Hillton.  River front home near Madison.

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. The space 2 separated bedrooms- one with a queen bed, and one with two full-size beds. Living room contains a sectional leather sofa. Guest access Guests will have access to the entire home and yard!

Campus Cottage: Cozy, Convenient, Captivating

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!

Studio apartment above Garage in downtown Madison

New June 2024! Full time Airbnb. Come stay at this newly renovated home in historic downtown Madison. This 3-bed/2-bath home is adjacent to Bicentennial Park and includes a fully stocked kitchen, washer & dryer, internet, keyless entry, front porch that overlooks the Ohio River and more. From the front porch of this home, enjoy the festivities of live concerts and Friday-night movies. You will enjoy easy access to everything Main Street offers from this centrally located home.

Bicentennial Park View

This 1197 square foot single family home has 2 bedrooms and 1.0 bathrooms. This home is located at 221 W 1st St, Madison, IN 47250.

221 W 1st St Madison, Indiana

$41,113

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