Vacation Home Rentals By Owner In Madison, IN

Come enjoy the best of both worlds in our beautiful historic town! Cypress Grove Inn is approximately 1 mile from our beautiful downtown area. Cypress Grove Inn gives you the peace of the country along with the sounds of nature. A short drive and you will enjoy Madison Main St., where numerous restaurants and retailers await you!brYour accommodations are approximately 1800-2000 square feet, the accommodations are half of the house, large outer deck with 2 fire pits, hot tub, and fishing if you choose.brIt provides privacy at its best!brConsisting of 2 bedrooms,each with Queen bed, one full bathroom, and separate area with a small fridge, coffeemaker, and snacks.brLiving room with dining table, smart tv, electric fireplace, indoor fountain. brCleaning fee-$75brbrOur accommodations provide spacious rooms, closets, and individual patio seating over looking a Spring fed pond fully stocked with fish-- bring your poles, and enjoy a rest in the hot tub! brOur sunrises and sunsets are amazing, and the views will take your breath away. You most likely will encounter deer, wild turkey, and many other sights. Bring your bikes, hiking gear, and take a peaceful walk around the property or at Clifty Falls State Park that is only 6 miles away, local wineries with beautiful landscapes, walk the beautiful river-walk, and enjoy some of Madison's Magical Musicians in our historic taverns or outdoor venues.brbrYour host and hostess Tom and Chandra Ferry will greet you upon your arrival!brCode locks are used and codes will be given prior to arrival. brFeel free to pull up to the main front door to unload your belongings. There is additional parking available on the west end of the driveway.brUnfortunately, at this time we are not handicap accessible, however access into home is one level. There are stairs to the rooms. brbrThe Cypress Grove Inn is truly unique as it was built in 1825.brA true historical home, exhibiting the original hardwood floors, muscat shots embedded in the original exterior and interior field stone, five acres of property for you to take walks, a full spring fed pond that is open for fishing , quick access to Madison downtown/ various landmarks., and patio areas to embrace the beautiful sunrise and sunsets.brbrThere is so much to enjoy here in Madison, IN.brCome enjoy the best of both worlds-- Cypress Grove Inn looks forward to accommodating you!brbrGetting around--brGolf cart rentals available downtown-Acree Alley Carts. brInquire with hosts- we are happy to set a reservation for you! brCab service available as well.brList of suggested places to visit is provided. brbr**Hot Tub is located on lower deck area. There are safety guidelines listed once checked in. brbr**Checkout procedure- please just text hosts once you have departed. (317-625-8311). brAll towels, sheets, trash hosts will take care of for you. brIf there is an excess of trash feel free to place in dumpster and the north end of the house ( front). brIf any damage had occurred please Inform hosts prior to departing. brbrThank you for staying with us!

The Cypress Grove Inn ~Madison, IN!
*5 Star hosts!

Madison, Indiana, United States

Bed

Bath

Sleeps

$234.6

You will be close to everything when you stay at this centrally-located home. This historical landmark was built by and located next to The Francis Costigan Historical Home. You will be steps away from the Broadway Fountain, downtown shopping, and only a few blocks from the majestic Ohio River. This three bed, 1/12 bath home boats tall ceilings and large rooms which makes it a great place to stay with family or friends.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

Madison, Indiana, United States

Bed

Bath

Sleeps

$185.27

Beautiful Ohio River Frontage views from EVERY room (even the bathroom if the door was open!). Newly remodeled. Rural setting but close to town-5 minutes. Quiet nights. Swing on the country porch watching river roll by. Super clean and cleanable historic home. Carport, Woods. Waterfront theme. Watch fireworks from the porch or master bedroom. Handmade local amenities-natural soaps & spa products by award winning Fountain Alley BodyCare in MadisonbrbrThe spacebrOn designated Scenic Highway. This home was once an early trading post with a ferry that would cross the Ohio River. It had gambling and was used back then for hourly or overnight stays. It sets outside city limits and besides the busy highway during the daytime hours, it’s quiet and peaceful. Boats welcome.brJust outside of historic Madison Indiana, a stellar community, on historic registry, and just a beautiful place to go with shopping and restaurants and a state park! brbrGuest accessbrWhole house (excluding laundry room), large west side yard, short wooded trail behind home. The highway gets busy, be careful! brbrOther things to notebrThe highway is close and busy in the day. Pulling in and out of the driveway should be exercised with extreme caution. Children and elderly, pets, should be watched to stay away from the busy highway.brANOTHER CAUTION: tall people be aware that the down stairs bathroom has a low clearance doorway, the stairway is low clearance, and a few beams throughout the home are low clearance. brbrThe sleeping arrangements are: there is one completely private room with a twin and full sized bed. The master bedroom- with king bed- one must go through to get to the private room with the 2 beds. There is a hide a bed couch in the great room. The master bedroom is the nicest room but again it is open to the guest bedroom so not super private but roomy and the best view with sliding doors. This master bedroom has no door but is upstairs. See photos

River Views from Every Room! Clean Fun, Secluded, but close to town. Pool table

Madison, Indiana, United States

Bed

Bath

Sleeps

$282.55

Newly remodeled, well furnished, spacious one story 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 make this a boaters dream.brbrShort drive to Clifty Falls State Park and Hanover CollegebrbrViews of the Ohio River and Madison bridge are beautiful from the front porch.brbrThis home is completely contactless. You 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 2 is the right 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.brbrLinens 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 at brhttps://www.vrbo.com/4277632 dateless=true

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

Madison, Indiana, United States

Bed

Bath

Sleeps

$431.25

Welcome to the Jefferson Off Main home. We are pleased to offer a spacious, historic home in the heart of downtown Madison. This 1900 historic house offers 4 bedrooms and is perfect for families, or groups. The Jefferson Off Main has 3 full bathrooms and 3 king size beds for your comfort. The 4th bedroom offers a double size bed as well. Full Cental air to keep you cool in the summer and 3 electric fireplaces to keep you warm during the colder months. But the best part about the house is how close we are to Main St. You won't have to drive to get to shopping and dining.

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Madison, Indiana, United States

4

Bed

Bath

8

Sleeps

$243.23

The Wadsworth House was built in the mid-1800s. It is a fully renovated and modern Shotgun house in a quiet part of town on the east side, walkable to all events, to the river, and to shops/boutiques on Main St. Some folks living around have been living in the area all their lives. The Wadsworth House is situated on a charming tree-lined street with lots of character. Besides being a family name, it is also named The Wadsworth House in honor of Henry Wadsworth Longfellow, whose poems I was forced to recite in the 5th grade! Hated it then, appreciate it now :)brbrOne of the original owners, a carpenter, moved into the house in 1907 and added the side hall onto the east side of this shotgun house, giving it the privacy needed for the family. He had immigrated from Germany and took a job working at the button factory in town. Hardwood floors, a modernized full kitchen with granite countertops, and king-sized beds with full tiled bathrooms make this house a comforting getaway.

The Wadsworth in National Historic District of Madison, Indiana.

Madison, Indiana, United States

Bed

Bath

Sleeps

$356

Welcome to this charming house in historic Madison Indiana. This amazing property features 3 bedrooms with 2 king beds and 1 queen bed, perfect for a group of guests looking for a tremendous stay. The 2 bathrooms are equipped with all the essentials you need, including a hair dryer and a shower. Kickback, relax, and enjoy everything Madison and our 1864 historic house has to offer.

Charming 3-bedroom house in lovely downtown Madison.

Madison, Indiana, United States

Bed

Bath

Sleeps

$180.76

Summary:brbrGet 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)brbr•Fast Wi-Fibrbr•Electric Fireplacebrbr.Two 55” Roku TVs, Complimentary YouTube TVbrbr•Keurig & Drip Coffee, K-cups, local coffee, tea, bottled waterbrbr.Paved driveway parkingbrbr.Gas BBQ grillbrbrbrbrThe Space:brbrYou'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. brbr 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. brbr Upon entering the house there are seven steps to go down to the main floor. Everything is on the main floor of the house. brbr 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. brbr Enjoy your stay at the Artist's A Frame.brbrbrbr4 Guests | 1 King Bed | 1 Queen Bed | 1 BathroombrbrbrbrGuest Access:brbrThe 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.brbrbrbrThe Neighborhood:brbrThis well established, quiet neighborhood is perfectly appointed near all of Madison's attractions.brbrbrbrOther Things to Note:brbrYou may see wildlife on the property including deer and squirrels.brbrbrbrInteraction with Guests:brbrI am available to offer assistance through platform messaging, or direct booking email.

The Artist’s A-Frame

Madison, Indiana, United States

Bed

Bath

Sleeps

$278

Experience the poetic intersection of art and mortality at The Raven. This stay is a tribute to Edgar Allan Poe & the beauty in death, where the macabre is met with elegance and the transient nature of life is celebrated through high-Gothic design.brSurround yourself with a collection of decor from intricate skull art to watchful ravens within a space that transforms darkness into a moody retreat. brIndulge in a stay that is as timeless as a memory and as hauntingly beautiful as a lost love.brbrLocated in Historic downtown Madison, Indiana, renovated 19th-century home equipped with modern amenities & four comfortable Queen-sized beds in 3 bedrooms. Each bedroom has a bathroom near or adjacent to the bedroom. Located near the Ohio River, easy access to downtown shops, restaurants, and nearby attractions like Clifty Falls State Park

Unique! Edgar Allan Poe inspired Gothic themed home in Madison

Madison, Indiana, United States

Bed

Bath

8

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

$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

$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

4

Bed

2

Bath

8

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