Vacation Rentals By Owner In Madison, IN

brIf you're looking for an ultimate log cabin retreat, then look no more. Francine's Log Cabin is a unique, small Authentic 18th century log cabin. The cabin site on 26 private acres surrounded by cedar trees, a pond and southern Indiana's rolling ridges with expansive views. Equipped kitchen with stone fireplace and hand-crafted cabinets. Cozy living room with vintage parlor stove, digital TV/DVD and sleeper sofa. Queen pillow top bed upstairs. large full bathroom. 2 covered porches, rocking chairs, porch swing, Hammock, Gazebo with outdoor napping bed. Fishing pond and outdoor shower. Beautiful sunsets and star gazing, relax and unwind here.br

Cabin

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Madison, Indiana, United States

Bed

Bath

4

Sleeps

$308.07

Stroll to Public Pool, Dining & Museums | Walk to Golf Cart Rentals | Shared Outdoor SpacebrbrDiscover small-town charm with a stay at this Folk Victorian home in the heart of Madison's Historic Landmark District! This vacation rental offers a covered porch for slow mornings and a shared fire pit for evening stargazing. With the Ohio Rivewalk, Broadway Fountain, and local festivals just steps away, you’ll experience the best of Indiana’s most beautiful river town. Secure your getaway today!brbr-- THE PROPERTY --brbrOUTDOOR LIVINGbr- Private covered porchbr- Shared yard & patio w/ dining tablebr- Shared wood-burning fire pit w/ grillbrbrINDOOR LIVINGbr- Smart TV, board gamesbr- Dining tablebr- Washer, dryerbr- Central A/C & heatingbr- Portable cribbrbrGOURMET KITCHENbr- Fully stocked w/ Le Creuset cookware, Breville sous vide equipment, new cooking tools & morebr- Gas stove, oven, dishwasherbr- Drip & Nespresso coffee makersbr- Toaster, microwavebrbrACCESSIBILITYbr- Single-story home, 1 small step for accessbrbrPARKINGbr- Free street parking (first-come, first-served)brbrADDT’L ACCOMMODATIONSbr- An additional studio property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Enjoy a walkable neighborhood filled w/ 19th-century architecture & riverfront charmbr- Walk to local boutiques, cafes & restaurantsbr- Walk to the Madison Chautauqua Festival of Art & Crystal Beach Aquatic Parkbr- Walk to Acree Alley Golf Cart Rentalsbr- 5 miles to Clifty Falls State Park for hiking & waterfallsbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 1 small step for accessbr- There is another bookable vacation rental on-site; other travelers may be present during your stay. The backyard and patio are shared amenitiesbrbrSECURITY CAMERA INFORMATIONbr- 3 exterior devicesbr- Location: front porch, backyard, garage doorbr- Coverage: street, backyard, alley

2nd Street Inn: Historic 1870s Gem Steps From Main

Madison, Indiana, United States

Bed

Bath

Sleeps

$412.85

The soaking tub downstairs is so spacious, some have called it an indoor pool. Whether that's true or not, it's a beautiful spot to spend some time in, while you're in Madison.brbrThe kitchen is outfitted by Williams Sonoma, made-in, and Caraway. The sheets are linen; comforters and pillows feathery and fluffy; towels and robes are made by Turkish Towel company. brbrEnjoy a vacation out of the ordinary and all that Madison has to offer at Stay Lello.

3-suite cottage spa (aaaah!) house—amenities galore, in historic Madison Indiana

Madison, Indiana, United States

Bed

Bath

Sleeps

$412.85

Welcome to this historic and beautifully decorated Main St home in Madison, IN that sleeps 8 guests comfortably with 4 bedrooms, 2 full and 2 half baths! Enjoy a fully equipped kitchen, coffee bar, games, fast WiFi, and plenty of space to relax. Steps from shops, dining, bars, the Ohio Riverfront, 6 minutes to Clifty Falls State Park and 12 minutes to Hanover College. Perfect for families, couples, and groups seeking charm, comfort, character, with the best Main St location.brbrFeaturing four beautifully designed bedrooms (2 king beds, 1 queen, and 1 full), and 4 bathrooms, this spacious Main Street home is the perfect retreat for relaxation and exploration. Step inside and you’ll be welcomed by thoughtful décor that blends modern comfort with historic Madison charm. This is a two-story home. There is a king and full bed downstairs and a king and queen bed upstairs, with bathrooms on both levels. brbrThis home offers everything you need for an unforgettable stay. Unwind in the roomy, stylish living areas, or prepare meals with ease in the fully equipped kitchen. Start your morning at the coffee bar, enjoy time together with the family-friendly games, and take advantage of the ample space to spread out and feel at home.brbrWhether you're strolling along the Ohio Riverfront, visiting local shops and restaurants just steps away, or exploring nearby attractions like Clifty Falls State Park and Hanover College, this centrally located Main Street escape delivers comfort, convenience, and the perfect Madison experience. brWe welcome all fur friends for an additional fee! If staying with your pet, please bring some pet waste bags with you. brbrStairs are required for second level bedrooms. There are two bedrooms (king and full sized bed) on the main level.brbr*Please note - we do allow early check-in and late checkout when our schedule permits, however there is a $25 an hour fee added to your stay prior. Our cleaners work very hard and have many houses to clean. This fee is charged to accommodate rearranging their schedule*

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

Madison, Indiana, United States

Bed

Bath

Sleeps

$151.73

This 2-bedroom cottage in Madison is perfect for your escape to a charming retreat. We are surrounded by the heritage trail that will lead to the river and within blocks of all the shopping and festivals. You will have the best of both worlds. Nature and relaxation along with connection with the historic district. The cozy bedrooms feature 1 full bed and 1 twin bed, ensuring a restful night's sleep for all guests. With a welcoming living room and a sofa bed for additional space, this enchanting property offers a comfortable stay. The bathroom amenities include a shower and a hairdryer for added convenience. We think our place will help you experience everything Madison has to offer. We have a nice relaxing private deck and perfect place for your pets with a dog door in the kitchen leading into a fenced area. All pets are welcome.

Cottage

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Madison, Indiana, United States

Bed

Bath

Sleeps

$127.71

Your cozy getaway awaits in Madison at this fantastic loft. With 2 bedrooms featuring a queen bed and a trundle bed, along with a bathroom equipped with a jetted bathtub and separate shower. This quaint retreat is perfect for guests looking for an enjoyable stay. Literally step out your door to all Madison has to offer. Festivals, wineries, restaurants, coffee shops and shopping. This loft is from the 1800s and is decorated with history in mind. And don’t forget the private deck just for you. We're happy to assist with any questions while you stay at our loft. We are within walking distance of all downtown Madison shops and within a mile from Clifty Park and a couple miles from Hanover College.brI am a native of Madison and love hosting. I want you to love your stay. You can always reach out with questions. I have been hosting successfully for over 7 years.

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Madison, Indiana, United States

Bed

Bath

Sleeps

$217.35

Get ready to relax in this 2-bedroom townhome in Madison. This quaint and welcoming property features 1 king bed, 1 sofa bed, and 1 queen bed, perfect for a small group of guests. With amenities like heating, iron, hair dryer, and AC, you'll feel right at home. The 2 bathrooms come equipped with a hair dryer and shower for your convenience. Kickback, relax, and enjoy everything Madison and our townhome has to offer.

Beautiful townhome just steps from Historical Downtown Madison

Madison, Indiana, United States

Bed

Bath

Sleeps

$164.48

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. 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!brbrEnjoy your morning coffee with a beautiful Main Street view in this cozy 1-bedroom apartment. The space offers a queen bed in the bedroom and a spacious 2-person sleeper sofa in the living room, comfortably accommodating up to 4 adults.brbrRelax in a thoughtfully curated space filled with cozy furnishings and modern styles, designed with you in mind. The fully equipped kitchen, complete with a coffee bar, is perfect for all your cooking and sipping needs. Additional amenities throughout the home ensure a fantastic experience during your stay. The Main St. Oasis is the perfect blend of relaxation and exploration.brbrOnce you arrive will you find a Welcome Book on the counter with recommendations, attractions, contact info, and more! Please note - stairs are required.

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Madison, Indiana, United States

Bed

Bath

Sleeps

$159.04

Your home away from home in Madison with 2 lovely queen bedrooms. This fabulous house offers a serene atmosphere perfect for unwinding after a day of exploring. Complete with a cozy living space, a fully equipped kitchen, and a modern bathroom with a shower, firepit, and a BBQ grill, our place is equipped for both long and short stays to make your holiday one to remember.

Charming 2-bedroom house with a river view in wonderful Madison

Madison, Indiana, United States

Bed

Bath

Sleeps

$360

Clean, comfortable 4BR hilltop home just minutes from Clifty Falls and downtown Madison. Sleeps 8 and is perfect for families, friends, or small groups looking for a relaxing home base. Enjoy Adirondack chairs, a gas fire pit, and grill after a day of hiking or exploring. Inside offers a full kitchen, dining space, cozy living room, coffee station, extra blankets, and 2 full baths so you can settle in and feel at home.

Clifty Falls Family Getaway-Sleeps 8--3 Miles to Historic Downtown & River Front

Madison, Indiana, United States

Bed

Bath

Sleeps

$202.98

Nestled in the charming downtown of the river-town of Madison, Indiana. This fully renovated historic building brings the modern amenities to character of old. Walk to all the best shops Madison has to offer, ride golf carts along the river, or hike through Clifty Falls state park. This boutique hotel will make your stay easy.brbrThe open-plan design includes a comfortable sleeping area with a king bed and a shower that offers a revitalizing start or end to your day.brbrDisclaimers: br- CONSTRUCTION on the third floor units takes place during the weekday working hours. This should only last until the end of September 2023. br- East Main Lofts is located downtown on the Main Street so road noise from the street can be heard. brbrWhat to expect:br- Two rolls of toilet paperbr- 2 sets of hand towels and bath towelsbrbrWhat shops and restaurants do we recommend: br- Madison Kitchen and Bakery is right down stairs for baked goods and breakfast on the weekends.br- The Attic is another Madison staple for lunch. I order a grilled chicken wrap with chips and their raspberry salsa is amazing. br- Fountain Alley Soaps features locally made soaps and other skin care products. I trust Sanya, the owner and operator to source her ingredients ethically and holistically. I especially love the honeycomb grapefruit and peace and calm scents. br- Uncommon Pizza has very yummy pizza. They have a lengthly and particular process to making their dough, and they bake their pizza in big wood-fired ovens. We all love the sweet Piggie pizza and fight over the leftovers. The sea salt bread sticks are delicious too.br- The Thomas Family winery is one of the most charming spots in town. It has an old-world pub aesthetic, and also has the best outdoor seating in town. They bake yummy crusty breads; feature common and unique cheeses and salamis; and make their own wine on-site. They offer colorful tasting experiences, and if you get to meet Steve and Elizabeth, the long-time owners and operators, they will make you feel like family.

East Main Lofts - Farmhouse 204

Madison, Indiana, United States

Bed

Bath

Sleeps

$300.2

Nestled in the charming downtown of the river-town of Madison, Indiana. This fully renovated historic building brings the modern amenities to character of old. Walk to all the best shops Madison has to offer, ride golf carts along the river, or hike through Clifty Falls state park. This boutique hotel will make your stay easy.brbrThe open-plan design includes a comfortable sleeping area with two king beds and a shower that offers a revitalizing start or end to your day.brbrDisclaimers: br- A remodel on the third floor units takes place during the weekday working hours, the noisy / dusty work is complete. This should only last until the end of September 2023. br- East Main Lofts is located downtown on the Main Street so road noise from the street can be heard. brbrWhat to expect:br- Two rolls of toilet paperbr- 2 sets of hand towels and bath towelsbrbrWhat shops and restaurants do we recommend: br- Madison Kitchen and Bakery is right down stairs for baked goods and breakfast on the weekends.br- The Attic is another Madison staple for lunch. I order a grilled chicken wrap with chips and their raspberry salsa is amazing. br- Fountain Alley Soaps features locally made soaps and other skin care products. I trust Sanya, the owner and operator to source her ingredients ethically and holistically. I especially love the honeycomb grapefruit and peace and calm scents. br- Uncommon Pizza has very yummy pizza. They have a lengthly and particular process to making their dough, and they bake their pizza in big wood-fired ovens. We all love the sweet Piggie pizza and fight over the leftovers. The sea salt bread sticks are delicious too.br- The Thomas Family winery is one of the most charming spots in town. It has an old-world pub aesthetic, and also has the best outdoor seating in town. They bake yummy crusty breads; feature common and unique cheeses and salamis; and make their own wine on-site. They offer colorful tasting experiences, and if you get to meet Steve and Elizabeth, the long-time owners and operators, they will make you feel like family.

East Main Lofts - Boho 203

Madison, Indiana, United States

Bed

Bath

Sleeps

$289.4

Nestled in the charming downtown of the river-town of Madison, Indiana. This fully renovated historic building brings the modern amenities to character of old. Walk to all the best shops Madison has to offer, ride golf carts along the river, or hike through Clifty Falls state park. This boutique hotel will make your stay easy.brbrThe open-plan design includes a comfortable sleeping area with a king bed, a full kitchen for preparing your meals, and a shower that offers a revitalizing start or end to your day.brbrDisclaimers: br- CONSTRUCTION on the third floor units takes place during the weekday working hours. This should only last until the end of September 2023. br- East Main Lofts is located downtown on the Main Street so road noise from the street can be heard. brbrWhat to expect:br- Two rolls of toilet paperbr- 2 sets of hand towels and bath towelsbr- 1 pod of dishwasher detergent for the kitchenbr- 1 roll of paper towels.brbrWhat shops and restaurants do we recommend: br- Madison Kitchen and Bakery is right down stairs for baked goods and breakfast on the weekends.br- The Attic is another Madison staple for lunch. I order a grilled chicken wrap with chips and their raspberry salsa is amazing. br- Fountain Alley Soaps features locally made soaps and other skin care products. I trust Sanya, the owner and operator to source her ingredients ethically and holistically. I especially love the honeycomb grapefruit and peace and calm scents. br- Uncommon Pizza has very yummy pizza. They have a lengthly and particular process to making their dough, and they bake their pizza in big wood-fired ovens. We all love the sweet Piggie pizza and fight over the leftovers. The sea salt bread sticks are delicious too.br- The Thomas Family winery is one of the most charming spots in town. It has an old-world pub aesthetic, and also has the best outdoor seating in town. They bake yummy crusty breads; feature common and unique cheeses and salamis; and make their own wine on-site. They offer colorful tasting experiences, and if you get to meet Steve and Elizabeth, the long-time owners and operators, they will make you feel like family.

East Main Lofts - Coastal 201

Madison, Indiana, United States

Bed

Bath

Sleeps

$293.23

Nestled in the charming downtown of the river-town of Madison, Indiana. This fully renovated historic building brings the modern amenities to character of old. Walk to all the best shops Madison has to offer, ride golf carts along the river, or hike through Clifty Falls state park. This boutique hotel will make your stay easy.brbrThe open-plan design includes a comfortable sleeping area with a king bed, a full kitchen for preparing your meals, and a shower that offers a revitalizing start or end to your day.brbrDisclaimers: br- CONSTRUCTION on the third floor units takes place during the weekday working hours. This should only last until the end of September 2023. br- East Main Lofts is located downtown on the Main Street so road noise from the street can be heard. brbrWhat to expect:br- Two rolls of toilet paperbr- 2 sets of hand towels and bath towelsbr- 1 pod of dishwasher detergent for the kitchenbr- 1 roll of paper towels.brbrWhat shops and restaurants do we recommend: br- Madison Kitchen and Bakery is right down stairs for baked goods and breakfast on the weekends.br- The Attic is another Madison staple for lunch. I order a grilled chicken wrap with chips and their raspberry salsa is amazing. br- Fountain Alley Soaps features locally made soaps and other skin care products. I trust Sanya, the owner and operator to source her ingredients ethically and holistically. I especially love the honeycomb grapefruit and peace and calm scents. br- Uncommon Pizza has very yummy pizza. They have a lengthly and particular process to making their dough, and they bake their pizza in big wood-fired ovens. We all love the sweet Piggie pizza and fight over the leftovers. The sea salt bread sticks are delicious too.br- The Thomas Family winery is one of the most charming spots in town. It has an old-world pub aesthetic, and also has the best outdoor seating in town. They bake yummy crusty breads; feature common and unique cheeses and salamis; and make their own wine on-site. They offer colorful tasting experiences, and if you get to meet Steve and Elizabeth, the long-time owners and operators, they will make you feel like family.

East Main Lofts - Haven 202

Madison, Indiana, United States

Bed

Bath

2

Sleeps

$181.13

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 (golf cart available for additional fee), 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.brbrOur 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.brbrDownstairs 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.brbrStep 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.

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison, Indiana, United States

Bed

Bath

Sleeps

$850.88

Madison Manor is one of the only homes in town featuring both a hot tub and multiple game rooms. With 2 adjoining townhouses, each with its own private entry, living room, and kitchen, this expansive home with vaulted ceilings is perfect for large groups, multiple families, reunions, and celebrations that call for space, comfort, and connection.brbrEnjoy vintage character and modern comforts; a patio with hot tub, fire pit, and grill; game rooms with a 3-in-1 mini pool/air hockey/ping pong table, a movie theater with projector and screen;, dartboard, poker set, and an impressive game selection; and a prime location in the heart of downtown Madison, Indiana — just steps from the Ohio River, shops, restaurants, wineries, and scenic walking paths.brbr———————————————————————————————————————————brWelcome to Madison Manor — two beautifully restored adjoining townhouses in the heart of downtown Madison, Indiana, just steps from the Ohio River, shops, restaurants, wineries, and scenic walking paths. Perfect for large groups, multiple families, reunions, and celebrations that call for space, comfort, and connection.brbr✨ Highlightsbr• Two 2-story adjoining Townhouses under one roof • Private entriesbr• 5 bedrooms • 4.5 bathroomsbr• Sleeps 16 — 12 guests + 4 small childrenbr• 4 Queens · Twin Bunkbed in pass-thru BR with open doorways and limited privacy · 2 Toddler mattresses · 2 Pack-n-playsbr• Ideal for multiple families, larger groups, and couplesbr• Walk to Downtown Madison & the Ohio Riverbr• Free street parkingbr• Two fully equipped kitchensbr• Ultra-fast WiFi • 6 Smart TVsbr• Washer & dryerbr• Patio • Hot tub • Fire pit • Gas grillbr• Two game rooms • Pool, air hockey, ping pong • Mini movie theater w/ screen & projector • Dartboard • Poker set • Board gamesbr• Golf cart rental (subject to availability)br• Quiet, well-mannered dogs welcome with prior approval • Pet fee appliesbrbr— The Details —brWelcome to Madison Manor, a rare whole-house downtown stay. Madison Manor I and II are two halves of the same Italianate-style home built in 1870, offering an unbeatable combination of location, character, and standout amenities — ideal for larger groups who want to stay together without feeling crowded. 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.brbrCurated 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.brbr Sleeping arrangements (sleeps 12 comfortably + 4 small children):brMadison Manor Ibr• Bedroom 1 (2nd floor): Queen bed, vintage charm, TV, storagebr• Bedroom 2 (2nd floor): Queen bed, calming natural light, TV, storagebr• Full bath with walk-in shower (2nd floor)br• Bedroom 3 (1st floor): Train-themed bunk room with ensuite full bathbrThis is a unique pass-through room with open doorways on each side, best suited for children rather than adults seeking full privacy.br• Pack ’n Play and toddler mattressbrbrMadison Manor IIbr• Bedroom 4 (2nd floor): Queen four-poster bed, TV, storagebr• Bedroom 5 (2nd floor): Queen bed, natural light, TV, storagebr• Full bath (2nd floor)br• Game Room / Living Room (1st floor): Two twin futonsbr• Full bath with walk-in shower (1st floor)br• Half bath (1st floor)br• Pack ’n Play and toddler mattressbrbrStep outside to a shared backyard oasis featuring:br• Pergola with café lightingbr• Hot tub for year-round relaxation (closed below 20°F)br• Fire pit for cozy eveningsbr• Gas grill and outdoor dining areabrbrAfter a day exploring Madison on foot — or by golf cart — return to a space that feels both special and comfortable.brbr Unbeatable Locationbr• 10-minute walk to downtown Madisonbr• 2-minute walk to the Ohio Riverbr• 5 blocks to boat ramp — wide on-street 1 block away for trailerbr• 10-minute walk to Milton–Madison Bridge walking pathbr• 10-minute drive to Clifty Falls State Parkbr• 15-minute drive to Hanover Collegebr• 10-minute drive to Madison HilltopbrYou’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.brbr— Why We’re Different —br• Hot tub — a rare amenity in Madisonbr• Two dedicated game rooms — also rarebr• Walk-to-everything convenience reduces event-day parking chaosbr• Convenient onsite golf cart rental (subject to availability)br• Perfect for multiple families and large groupsbr• Historic charm paired with modern comfort upgradesbr• Multiple workspaces for remote workersbr• Patio + hot tub + fire pit + outdoor seating for group meals or downtimebr• Excellent for Regatta, Chautauqua, Hanover College visits, and festivalsbr• Room-darkening curtains, ear plugs, & Dohm machine for restful sleepbrbr Family-Friendly Featuresbr• Two of each: highchairs, baby baths, Pack ’n Plays, toddler mattressesbr• Two game rooms with distinct entertainment for all agesbr• Bathtubs (Manor I main level, Manor II upper level)br• Quiet neighborhood ideal for evening walksbrbr Pet-Friendly Perksbr• Medium crate and dog bedbr• Food and water bowlsbr• Waste bags conveniently provided near the front doorbr• Patio tetherbr• Sofa coverbrbr Sustainability — Lower Your Travel Footprintbr• Local coffee ☕ with reusable filters br• Fresh, local flowers (in season)br• Recycling providedbr• Refillable dispensers with shampoo, conditioner, and body washbr• Eco-friendly toiletries like bamboo toothbrushesbr• Eco-friendly cleaning products + “free & clear” detergentbr• WiFi-enabled thermostatbrbr House RulesbrQuiet hours: 10pm–8am (City of Madison ordinance)brNo parties or unauthorized eventsbrOnly registered guests permitted overnightbrDogs allowed with prior approval and pet feebrNo smoking or vaping anywhere on the propertybrPlease remove shoes indoorsbrCheck-out: simple list provided in homebrHot tub rules posted onsitebrPet rules: (1) Must use sofa cover provided; (2) pets not permitted on any other furniture (3) Leash required on the patio.

Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16

Madison, Indiana, United States

Bed

Bath

Sleeps

$431.68

505 W Main Street – Historic Downtown Madison, IndianabrbrSleeps 6 | 3 Bedrooms | 2.5 Baths | High-Speed Wi-Fi | Walk to Riverfront & ShopsbrbrRelax and reconnect in this beautiful historic end-row townhouse in the heart of Madison, Indiana. Just steps from Main Street shops, restaurants, and the scenic riverfront, Sycamore on Main offers the perfect blend of modern comfort and old-world charm. Enjoy brand-new, high-quality furniture and beds throughout the entire home.brbrThe Spacebr • Bedrooms (Sleeps 6)brPrimary Suite: 1 King bedbrBedroom 2: 1 Queen bedbrBedroom 3: 2 Twin bedsbr • Bathroomsbr2 full baths (both with showers) plus 1 half bath for convenience.br • Living & DiningbrBright, welcoming living room with Smart TV and popular streaming services. Family-sized dining table plus comfortable seating areas. Front entrance historic sitting room. Sun room with games for children or just relaxing. br • KitchenbrFully stocked for real cooking—full-size appliances, cookware, and all basic kitchen utilities.br • LaundrybrWasher and dryer with detergent provided.br • Comfort FeaturesbrCentral heating and cooling, ceiling fans in key rooms, and high-speed Wi-Fi for work or play.brbr⸻brbrOutdoor LivingbrbrRelax in the backyard patio and covered seating area, perfect for morning coffee or evening conversations.brbr⸻brbrFamily-Friendly TouchesbrbrPack ’n play, high chair, plus games and books make family travel easier and more fun.brbr⸻brbrParking & Accessbr • Street Parking: Usually at least one space directly on Main Street in front of the home; additional parking on Elm Street just steps away.br • Smart Lock Check-In: Secure, contactless entry with your unique code.br • Check-in: 2:00 PM | Check-out: 10:00 AMbrbr⸻brbrLocation HighlightsbrbrSet right on Main Street in Madison’s celebrated Historic District:br • Ohio Riverfront Walk and Lanier Mansion are just a short stroll away.br • Boutique shopping, cafés, and local restaurants line the surrounding blocks.br • Quick 5-10 minute drive to Clifty Falls State Park with waterfalls and hiking trails.brbr⸻brbrHouse Rulesbr • No petsbr • No smoking, candles, or eventsbr • Quiet hours 9 PM – 8 AM to ensure a peaceful stay for everyone.brbr⸻brbrWhy Guests Love 505 W Mainbr • Prime downtown location—park once and explore on footbr • Fresh, elegant furnishings and beds throughoutbr • Thoughtful extras for families and long-weekend getawaysbrbrCome experience the best of Madison, Indiana—where historic charm and modern comfort meet at 505 W Main Street.

Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront

Madison, Indiana, United States

Bed

Bath

Sleeps

$281.75

Newly remodeled, well furnished, single story spacious home in the heart of everything going on in historic downtown Madison, Indiana.brbrSteps from the river puts you on the doorstep of the Riverwalk and all the festivals on Vaughn Dr.brbrJust 2 blocks to Main St makes an easy walk to all of the shopping, dining and events on Main St.brbrClose to the public boat ramp and ample room for boat parking makes this one a boaters dream.brbrShort drive to Hanover College and Clifty Falls State ParkbrbrViews of the Ohio River and Madison bridge are beautiful from the front porch.brbrYou will receive a door code the day before your stay for a contactless entry.brbrThis home is a duplex. Inside the front door is a foyer area which contains the front door to the home. Riverside Retreat is the left side of the duplex featuring 3 bedrooms, 2 full baths, spacious living room, workspace, laundry room, full size dining room and large well stocked kitchen. Linens and towels are included along with a limited supply of other essentials such as coffee, body wash, shampoo, conditioner, hand soap, toilet paper, dish soap and paper towels.brbrConsider renting the entire duplex to have a 6 bedroom/4 bathroom home under one roof. Check out Riverside Retreat 2 at https://www.vrbo.com/4182868 dateless=true

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

Madison, Indiana, United States

Bed

Bath

Sleeps

$365.13