Home Vacation Rentals By Owner In Madison, IN

Showing 20 Of 82 Vacation Rentals
Slider Thumb
Exceptional(1)

$711.45

/ Nightly
Private Vacation Home

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

Madison, Indiana, United States

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— Highlights —br• Two 2-story adjoining Townhouses under one roof • Private entriesbr• 5 bedrooms • 4.5 bathroomsbr• Sleeps 16 — 12 guests + 4 small children)br• 4 Queens · Twin Bunkbed in pass-thru BR with open doorways and limited privacy · 2 Toddler mattresses · 2 Pack-n-playsbr• Ideal for families, 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 young 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 / Common area (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 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 propertybrShoes off 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.
Bed 5

Bed

Bath 4

Bath

Sleep 16

Sleeps

Slider Thumb
Exceptional(27)

$207.0

/ Nightly
Private Vacation Home

The Artist’s A-Frame

Madison, Indiana, United States

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.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(17)

$196.65

/ Nightly
Cabin

Cabin on the Ridge: The Sequel

Madison, Indiana, United States

Summary:brbrWelcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. brbrbrbrThis is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as The prettiest small town in the Midwest or chase waterfalls at Clifty Falls State Park (25 minutes).brbrbrbr•Fast wifibrbr•Roku TVbrbr•Keurig (K-Cups Available)brbrbrbrThe Space:brbrMeticulously designed with you in mind. You’ll be greeted by an impressive great room that boasts an open floor plan with brbrsoaring vaulted ceilings and tall windows that flood the space with natural light.brbrbrbrThe cozy, modern kitchen is fully equipped to meet all your needs, with all the comforts of home. brbrbrbrTake time to relax and enjoy the spacious balcony from the bedroom with a cup of coffee or glass of wine, while gazing at the stars or sunset.brbrbrbrFor nights when a chill is in the air curl up next to the electric fireplace for a movie or nightcap. This space boasts both charm and comfort; enjoy your stay at Cabin on the Ridge: The Sequel.brbrbrbr2 Guests | 1 Queen Bed | 1 BathroombrbrbrbrThe Neighborhood:brbrThe cabin is located in a remote area, surrounded by an Amish Community. The only noise you may encounter is the occasional trot of a horse and buggy down the gravel road.brbrbrbrGetting Around:brbrThe cabin is located on a gravel road, please drive slowly. I supply directions to Madison in my guidebook at the cabin. Please do not use GPS to get to Madison, as it may not take you the most direct route.brbrbrbrInteraction with Guests:brbrI am available to offer assistance through platform messaging, or direct booking email.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(15)

$216.2

/ Nightly
Cabin

Cabin on the Ridge

Madison, Indiana, United States

Summary:brbrThis is the perfect destination for those who want to getaway yet enjoy the luxuries of nearby amenities such as Belterra Casino Resort (20 minutes), Kentucky Speedway (30 minutes) and Historic Downtown Madison (25 minutes), recognized as “The prettiest small town in the Midwest” by Ladies Home Journal and “Best Preserved Town in the Midwest” by the Chicago Tribune. brbrbrbr•Fast wifibrbr•Roku TV/Streaming servicesbrbr•Keurig (K-Cups Available)brbrbrbrThe Space:brbrYou’ll be greeted by an impressive great room that encompasses both the family room and fully equipped kitchen. Soaring vaulted ceilings and tall windows flood the space with natural light, with views of wooded seclusion. brbrbrbrTake time to relax and enjoy the full-length scenic covered-porch, with a cup of coffee or glass of wine. For nights when a chill is in the air curl up next to the electric fireplace for a movie or nightcap. This space boast both charm and comfort; enjoy your stay at Cabin on the Ridge.brbrbrbr4 Guests | 2 Queen Beds | 2 BathroomsbrbrbrbrGuest Access:brbrGuests have access to the family room, kitchen, primary bedroom, primary bathroom, guest bedroom, guest bathroom and loft. Guests do not have access to garage.brbrbrbrOther Things to Note:brbrYou may encounter wildlife on the property including deer, squirrels, turkey and more!brbrbrbrInteraction with Guests:brbrI am available to offer assistance through platform messaging, or direct booking email.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(9)

$202.98

/ Nightly
Apartment

East Main Lofts - Farmhouse 204

Madison, Indiana, United States

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.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(6)

$418.6

/ Nightly
Apartment

East Main Lofts - Haven 202

Madison, Indiana, United States

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.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb

$391.52

/ Nightly
Private Vacation Home

#209 Kings, River View, Deck, Bicentennial Park

Madison, Indiana, United States

General’s Quarters (209) is situated steps from the Ohio River. This renovated 3-level historic (circa 1830) home is a perfect (and spacious) gathering place for families and friends. brbrWe're located near all the festival action (Bicentennial Park) and easy walking distance to Main Street and bars and restaurants. Clifty State Park is a quick drive to the west side of town.brbrGQ includes 4 bedrooms (2-King Suites, 2-Queen) and Queen sleeper sofa in the living room.brbrTwo king bedrooms are located on the top floor with the washer and dryer and each has its own full bathrooms. The two Queen bedrooms are on the bottom floor with walkout access to the backyard and additional parking (ideal for anyone that doesn't do stairs). These bedrooms share a full bath. All bedrooms include a 43 flatscreen TV.brbrThe living/dining/kitchen areas are located on the middle floor and include all the comforts of home - a 75 TV, access to the back deck, workspace with a standing desk, charging station, Bluetooth speaker, and games for hours of entertainment. The deck is ideal for watching the river and enjoying the fresh air. A full-length glass door to the deck provides river views year-round.brbrFurnished with a mixture of antiques and modern furniture you’ll find General’s Quarters to be a great home away from home. Enjoy a great family gathering with plenty of room to make memories to last a lifetimebrbrYou'll have access to the entire house.brbrWe are available for any questions you have before, during and after your stay.brbrGeneral's Quarters is located right by Bicentennial Park (Center of town) between the river and Main Street. You'll be able to walk out your door to Main Street and all the festival action.brbrDowntown Madison is a great walking town or if you prefer you can rent a golf cart. Getting around is easy. There is also plenty of parking at General's Quarters - street and in the back (2 reserved spots).
Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(9)

$418.6

/ Nightly
Apartment

East Main Lofts - Coastal 201

Madison, Indiana, United States

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.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(8)

$465.76

/ Nightly
Apartment

East Main Lofts - Boho 203

Madison, Indiana, United States

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.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(47)

$277.88

/ Nightly
Private Vacation Home

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

Madison, Indiana, United States

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!
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(9)

$269.37

/ Nightly
Private Vacation Home

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

Madison, Indiana, United States

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
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(20)

$218.97

/ Nightly
Private Vacation Home

East End River Retreat: Dogs Welcome!

Madison, Indiana, United States

Walk Across Ohio River | Perks for Pups | Golf Cart | Coffee & Tea StationbrbrHistoric 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!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrINDOOR LIVINGbr- 3 Smart TVs, DVD players, DVDsbr- Board games, puzzles, books, CD player, CDsbr- Electric fireplacebr- Dining tablebr- Work desk (bedroom 1)br- Portable deskbrbrOUTDOOR LIVINGbr- Covered back patio, outdoor dining setbr- Fenced-in yard (15'x40')br- Front porch w/ 2 chairsbr- Golf cart (waiver required)brbrKITCHENbr- Dishwasher, refrigerator, stove/oven, microwavebr- Keurig coffee maker, coffee & tea, flavored syrups, cream & sugar, mugs & to-go cupsbr- Spices, toaster, blender, Crockpot, air fryerbr- Cooking & baking basics, dishware & flatware, trash bags & paper towelsbrbrGENERALbr- Central A/C, gas heatingbr- Towels & linens, complimentary toiletries, hair dryer, lap blanketsbr- Washer & dryer, iron & board, hangersbr- One-medium sized dog crate, dog dishes, pet throw blankets, waste bags, welcome treatbr- Free WiFi, keyless entrybrbrFAQbr- 3 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story home, 3 steps down to walkway + 1 additional step to enterbr- 1 interior step to access primary bedroom, bathroom & laundry roombr- Uneven flooring in entrywaybrbrPARKINGbr- Driveway (2 vehicles, behind property)br- Free street parkingbr- Free public parking throughout the citybrbr-- THE LOCATION --brbr- Walking distance downtown (designated as a National Historic Landmark): shops, cafes, restaurants, bars & grills, coffee houses, wineries & breweries, riverwalkbr- 1 mile to Heritage Trail & Madison Riverfront Dog Parkbr- 0.5 miles to Milton-Madison Bridge (Indiana/Kentucky state line)br- 0.6 miles to Ohio River boating accessbr- 5 miles to Clifty Falls State Parkbr- 1 mile to Lumber Mill Antique Mallbr- 27 miles to Belterra Casino Resortbr- 61 miles to Louisville Int'l Airport & 69 miles to Cincinnati/Northern Kentucky Int'l Airportbrbr-- 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 smoking or vapingbr- Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 2 max)br- Please crate dogs when left alone at the house. One medium-sized crate will be providedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The main point of entry is a side entrance which may be accessed from the front or rear of the propertybr- 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 yardbr- 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 housebr- A waiver is required prior to using the golf cartbr- Please note that the full bathroom can only be accessed through bedroom 1br- 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
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(63)

$169.07

/ Nightly
Private Vacation Home

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

Madison, Indiana, United States

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
Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps

Slider Thumb
Exceptional(2)

$435.88

/ Nightly
Private Vacation Home

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

Madison, Indiana, United States

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.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Madison