Home Vacation Rentals By Owner In Madison, IN

Showing 60 Of 64 Vacation Rentals
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Exceptional(22)

$243.8

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Private Vacation Home

Historic Row House in the heart of downtown Madison

Madison, Indiana, United States

About this space:brModern flair with antique charm sets this home apart! Located on a quiet street in the heart of historic downtown Madison, this fully renovated 1830s Row House has you steps away from everything! Whether it's a festival or fall colors, a boat race or car show on the riverfront, a micro brewery or winery, antiquing or historic tour, hiking Clifty Falls or simply just getting away, we have the location for you. *HVAC system includes whole-house air purifier. Max of 4 guests, adults only.brThe space:brFrom the morning light flooding through the front windows to welcome the day, to the fire bowl in the private courtyard in the back to bring it to a close, this historic home with modern flair provides everything you need to create wonderful memories each day of your stay. The restored, original hardwood floors make it feel like you are walking on history. Curl up on the couch in the living room with a book and enjoy the replicated coal-burning fireplace. A fully equipped kitchen (including Keurig, coffee, tea, water) and washer/dryer unit add all the conveniences of home. *For your safety, a whole-house air purifier that kills 99% of viruses has been installed with the new modern HVAC system controlled by Ecobee. The calendar only opens up three months in advance. If you are interested in extended stays message owner to check availability and special pricing.brGuest access:brEntire home and back courtyard
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Sleep 4

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$242.56

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Apartment

1 Block to Main St: 'Second Street Carriage House'

Madison, Indiana, United States

Exposed Brick Interior | 1,000 Sq Ft | Shared Outdoor Dining Area | Walk to Riverfrontbrbr1870s heritage meets modern living at this studio vacation rental in the heart of downtown Madison! Enjoy a home-cooked breakfast in the lofted living space before exploring nearby shops and museums or embarking on a hike through Clifty Falls State Park. After dinner in town, stroll the waterfront at sunset, then return home to unwind. Your timeless Indiana escape starts at 'Second Street Carriage House!'brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Studio 1st floor: 1 king bedbr- Studio 2nd floor: 2 twin bedsbrbrPROPERTY PERKSbr- Shared patio & yard, wood-burning fire pit w/ grillbr- Outdoor dining & seatingbr- Smart TVbr- Board gamesbr- Designated workspacebr- Dining table, dishes & flatwarebrbrKITCHENbr- Stove/oven, refrigerator, microwavebr- Nespresso coffee maker (starter pods provided), toasterbr- Cooking basicsbrbrGENERALbr- Central heating & A/C, ceiling fansbr- Linens/towels, hair dryerbr- Free WiFibrbrFAQbr- 3 exterior security cameras (facing out)brbrACCESSIBILITYbr- 2-story house, step-free entrybr- 1st-floor bed & bathroombr- Main living space & kitchen on 2nd floorbrbrPARKINGbr- Free street parking (first-come, first-served)brbrADDT’L ACCOMMODATIONSbr- An additional 2-bedroom 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- Located in the heart of Madison’s historic district, just steps from shops, galleries, restaurants & the scenic riverfrontbr- A few blocks to Lanier Mansion State Historic Site, Broadway Fountain, Bicentennial Park & Crystal Beach Aquatic Parkbr- 2 miles to Hanging Rockbr- 5 miles to Clifty Falls State Parkbr- 18 miles to Big Oaks National Wildlife Refugebr- 55 miles to Louisville International Airport & 68 miles to Cincinnati/Northern Kentucky International 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 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 2-story home offers step-free entry, with a bed and a bathroom on the 1st floor. The main living area and kitchen are on the 2nd floorbr- There is another bookable vacation rental on-site; other travelers may be present during your stay. The backyard and patio are shared amenitiesbr- Your safety matters. This property features 3 exterior security cameras mounted on the exterior of the house and garage, facing the exterior gates and the alley spaces behind the home. The cameras do not look into any interior spaces. The cameras record video when activated by motion
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Bath 1

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Sleep 4

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Exceptional(24)

$224.28

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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
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Sleep 4

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Exceptional(26)

$199.07

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Cabin

Cedar Rustic Cabin at Lost Trails

Madison, Indiana, United States

Nestled among four other cabins thoughtfully placed across 45 acres of wooded forest, this cabin offers a peaceful retreat just minutes from historic downtown Madison. Walking trails, tranquil ponds, and frequent wildlife sightings create a calm, relaxing setting away from the pace of everyday life.brbrbrbrThe cabin features a full kitchen, washer and dryer, and a comfortable living area with a double recliner, making this one-bedroom retreat ideal for couples or individual travelers. A wraparound deck provides comfortable seating and overlooks two nearby water features, offering a quiet place to unwind and enjoy the natural surroundings.brbrbrbrThe spacebrbrThis one-bedroom cabin features a full kitchen, washer and dryer, and a comfortable living area with a double recliner and gas fireplace—ideal for couples or individual travelers seeking a quiet, relaxing stay.brbrA wraparound deck and covered front porch provide comfortable seating with views of two nearby water features, including a small serenity pond and waterfalls. The cabin is equipped with modern amenities throughout, including new furnishings, two smart TVs, and high-speed, cable-based Wi-Fi. An outdoor gas grill, dining table, and chairs make it easy to enjoy meals outside.brbrThe kitchen is fully equipped with cookware, utensils, pots and pans, a refrigerator, electric stove, microwave, a standard 12-cup coffee maker with filters, a Keurig coffee maker with K-cups, sweeteners, and creamers. Starter supplies such as paper towels, dish soap, dish towels, trash bags, and basic kitchenware are provided.brbrThe bedroom includes a comfortable queen-size bed and HDTV.brbrThe full bathroom features a stand-up shower and includes fresh towels, shampoo, conditioner, body wash, hand soap, and starter toilet paper.brbrA private parking space is located adjacent to the cabin for convenience.brbrThe PropertybrbrThe cabin is situated on a 45-acre wooded property that includes walking trails and two small ponds. Trails range from gently sloped to moderately steep, and wildlife sightings—such as deer, squirrels, turkeys, and a variety of birds—are common throughout the property.brbrDistances to Nearby Destinations and EventsbrbrHistoric Downtown Madison – 5.3 miles (7 minutes)brbrMadison Hilltop Shopping District – 1.9 miles (4 minutes)brbrClifty Falls State Park – 5.3 miles (12 minutes)brbrHanover College – 11 miles (20 minutes)brbrBelterra Casino – 33 miles (43 minutes)brbrMadison Regatta – 5.3 miles (7 minutes)brbrMadison Ribberfest BBQ & Blues – 5.3 miles (7 minutes)brbrMadison Chautauqua Festival of Art – 5.3 miles (7 minutes)brbrNorton KDH Hospital – 1 mile (2 minutes)brbrLouisville, KY – 54 miles (1 hour 10 minutes)brbrCincinnati, OH – 74 miles (1 hour 26 minutes)brbrColumbus, IN – 45 miles (58 minutes)brbrIndianapolis, IN – 99 miles (1 hour 46 minutes)brbrbrbrGuest accessbrbrCheck-in: 4:00 PM (Eastern Time)brbr Check-out: 11:00 AM (Eastern Time)brbrAccess to the cabin is provided via a secure lockbox. The access code, directions, and cabin-specific information will be sent to guests within 24 hours of check-in.brbrOther Things to Note – Property PoliciesbrbrPetsbrbrPets are not permitted. Evidence of an unauthorized pet will result in a $300 cleaning fee.brbrSmokingbrbrSmoking is strictly prohibited on the property. Smoking is prohibited on porches, decks and patio areas. Smoking is not allowed in wooded or forested areas. Evidence of smoking, including odor, will result in a $200 fee.brbrChildrenbrbrThis property may be suitable for children under 12 years of age; however, children must be supervised at all times on porches, decks, trails, and near ponds or other outdoor features.brbrSafety & EmergenciesbrbrSmoke alarms and fire extinguishers are installed in all cabins. Guests agree not to tamper with or disable these devices. In the event of an emergency, guests must call 911 immediately and notify the Host as soon as reasonably practicable.brbrFire Safetybrbr Candles and indoor fires are not permitted. Please ensure the stove and fireplace are turned off when not in use. Fires are allowed only in the designated fire pit. Fires outside the fire pit are strictly prohibited. Due to the wooded setting, guests may not ignite fires or smoke elsewhere on the property.brbrIllegal ActivitiesbrbrIllegal substances and activities of any kind are strictly prohibited on the premises.brbrNoise & Quiet HoursbrbrGuests and visitors must keep noise to a minimum to respect neighboring cabins and properties. Quiet hours are observed between 11:00 PM and 8:00 AM, including during arrival and departure.brbrParties & EventsbrbrParties, gatherings, or events of any kind are not permitted.brbrVisitorsbrbrNo unregistered guests may stay overnight. Guests may have up to two daytime visitors during the stay. Overnight visitors are not allowed under any circumstances.brbrDamagesbrbrGuests are responsible for any damage to the cabin or property during their stay, including accidental damage. Costs for repairs or replacements will be charged as necessary.brbrRestricted AreasbrbrGuests may not enter other cabins or buildings on the property. These areas are strictly off-limits.brbrCabin RulesbrbrEach cabin includes posted rules and usage information that supplement these policies. A copy may be provided upon request prior to booking.
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Sleep 2

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Exceptional(15)

$313.95

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Private Vacation Home

Newly renovated, walkable, historic 4-bedroom house in bustling Madison.

Madison, Indiana, United States

Located in the Madison Historic District, close to everything when you stay at this centrally-located home. This gorgeous newly renovated home is located just a few blocks of bustling Madison Main St, the perfect place to stay w family/friends. well appointed kitchen, pots/pans/baking dishes/30+spices, cooking utensils, W/D, Free Reliable WiFi, dedicated workspace/desk/office chair, Smart TVs in 5 rooms, premise parking, Infant/Kid Friendly, Pet Friendly, 1 King, 2 Queens & 1 full futon-4th Bed.brbrKitchen: Fully equipped kitchen, 30 spices, olive oil, veg oil, baking powder, baking soda, pots/pans, baking sheets, muffin pan, large variety of utensils, blender, toaster, microwave, stove tea pot, water pitchers for lemonade/tea etc., glass & plastic drink cups, tall & short, 12 person corelle plate set, kids forks/spoons, standard & Keurig coffee makers with a variety of k-cup & ground original coffees/flavored coffees/tea-including tea bags & decaf coffee, flavored & original creamers & sweeteners. brbrBedrooms: 1 king bed, 2 queen beds, and 1 full futon (with thick mattress topper), portable fans on every nightstand, ceiling fans in each bedroom, ear plugs in the nightstands, several pillows to choose from, extra blankets & blackout curtains. Closets have hangers available for your use. 2 Pack n plays are available for your use- 1 is in large bathroom closet and one is in the king bedroom. Pack n play sheets are kept in the large bathroom closet. Smoke detectors & CO2 Detectors.brbrBathrooms: The 3 bathrooms are equipped with everything you need including hair dryers, shampoo/conditioner/body wash, shower/bathtub, forgot something baskets(razors/toothbrush/ear plugs/toothpaste & more), plenty of towels, hand towels, washcloths, makeup removal washcloths & hair dryers in every bathroom. brbrLiving Room: Very Cozy living room also with a smart TV, streaming your personal favorites, ceiling fan, 6 input iphone/android charging station.brbrDining Room: Large dining table perfect for meals, playing cards/games, etc. High chair & infant activity table is kept in the dining room. brbrDedicated Private Work Space: Take advantage of a quiet place to work or read when needed, in our library. Our library houses a variety of media detailing the history of Madison, Indiana, including art festival prints, old post cards, history books, etc. The library also contains the downstairs thermostat. brbrFuton Bedroom/Movie Room: Movie room w a variety of adult & child DVD's, 55 smart TV, children's books/games, infant/toddler activity cube. brLaundry Room: Washer/Dryer, Iron & Ironing Board, Steamer with distilled water available, Broom/Dust Pan.brbrParking: This home has an attached carport to the entry door, additional street parking available as well, brbrMADISON, INDIANA is known as the “City of Music” and keeps a packed event schedule to include hydroplane racing, multiple food, music & fun festivals, art festivals, wineries/breweries, brand new community pool complex that preserved the 1938 “seashore” design while adding more modern features - Crystal Beach Aquatic Park that boasts 2 waterslides, an activity tower for all abilities, diving board, wet deck, lazy river, lap lanes & water fitness classes (daily public swim hours during the season). Accessibility: the pool complex is designed to serve individuals of all abilities. brbrFood & Specialty Shops: You will also enjoy local family owned restaurants with amazing menu’s, coffee shops, creperie, ice cream shop, chocolatier and other specialty shops, in addition to the more familiar chain restaurants & stores up on the hilltop. brbrClifty Falls State Park & Nature Center: offers it’s own educational events/activity hiking trails/family fun events/women’s groups schedule. brbr3 Dog Park Options: Madison also offers the popular Lykos Riverfront Dog Park-fenced in area along the riverfront, that has separate spaces for large and small dogs. Secondly, Oakhill Dog Park on the hilltop-is a newly renovated park and is fenced in area with agility equipment. Third, Madison has Me and My Dog Park that offers private bookable spots available (east side of Madison). www.Bringfido.com brbrLanier Mansion State Historic Site- Known for it breathtaking Greek Revival Architecture and rich history. Tickets and tours available. brbrMadison offers so much more for everyone to enjoy. We are thankful for our guests and hope you enjoy your time in Madison and at our charming house, Mulberry Manor.
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$225.4

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Apartment

Best downtown location! Stablemasters Quarters is awarded winning! Come see why…

Madison, Indiana, United States

We have been awarded Best Place to Stay in Madison along with multiple other awards! brbrThis historic building was originally one of the city’s horse stables and has recently been converted into apartments. The new furnishings, bathrooms, luxury linens, towel warmer and a complete kitchen will be appreciated yet the historic charm is blended within. brbrThis fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the midwest”. Chicago Tribune says it’s “the best preserved midwest town.brbrAnd, USA TODAY awarded Madison as the BEST SMALL TOWN in the Midwest! Our building was also featured in 3 page article in the Louisville Courier Journal.brbrThis circa 1860 historic building originally was one of the city’s main stables. It’s now a blend of barnwood contemporary and vintage charm with so many amenities! brbrNew renovations, large gathering area and luxury furnishings will leave you wanting to stay longer. Come see why guests say they don’t want to leave!!brbrThis unit is on the main floor with a very easy entry There is also a laundry area. We provide baby and children supplies as well as portable chairs for your use during music festivals and other festivities. We are located at the start of the festivals, right on Broadway Street! The seasonal farmer's market is just across the street on Saturday mornings.brbrWe will also send you a list of recommendations and venues for live music before your arrival. brbrYou will see that we have the BEST downtown location!brbrWe are centrally located in the best part of downtown and in walking distance to most places.brbrOur Livery Loft apartment is another award winning unit and can sleep 5 more guests. It is located directly above Stablemaster's Quarters. We will soon have another unit available so we can then sleep up to 13 guests.brbrYou will be pleasantly surprised by all the amenities we provide and soon see why our guests often say we are their best vacation rental experience. brbrFeel free to read our years of 5 star reviews.
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Bath 2

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Exceptional(12)

$404.53

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Private Vacation Home

Madison Manor I | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

Madison, Indiana, United States

Madison Manor I is a spacious historic townhouse just 2 blocks from the Ohio River, 5 blocks to the boat ramp, & a short walk to charming downtown Madison. One of the only homes in town with both a hot tub and game room, it sleeps up to 8 and is perfect for families & small groups.brbrEnjoy vintage character, modern comforts, a shared patio with hot tub, fire pit & grill, plus air hockey, pool, ping pong, & more.brbrMadison Manor I adjoins Madison Manor II—book both homes together for larger groups. You may hear guests on the other side. Quiet hours are 10pm-8am. Earplugs and white noise machines are provided for your comfort & convenience.brbr✨ Highlightsbr• 2-story Townhouse • Private entrance • See layout photobr• 3 bedrooms • 2 bathroomsbr• Sleeps 8 (6 guests + 2 small children) · 2 Queens · Twin bunkbed in pass-thru room with open doorways and limited privacy · Toddler mattress · Pack-n-Play br• Ideal for families, groups, and couplesbr• Walk to Downtown Madison & the Ohio Riverbr• Free street parkingbr• Fully equipped kitchen • Washer & dryer in shared laundry roombr• Ultra-fast WiFi • 3 Smart TVsbr• Patio • Hot tub • Fire pit • Gas grill (shared amenities)br• Game room • Mini pool table/air hockey/ping pong • Board gamesbr• Golf cart rental (subject to availability)br• Quiet, well-mannered dogs with prior consent • Pet fee appliesbrbr— The Details —brThis Italianate-style townhouse built in 1870 offers a rare combination of prime location, architectural character, and standout amenities. Whether you’re visiting for a weekend getaway, a family trip, or an extended stay, Madison Manor I is designed for relaxation, connection, and memorable experiences. Inside, historic charm meets modern comfort with exposed brick and thoughtful décor. The well-equipped kitchen includes pantry basics and everything you need for easy meals at home.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 6 comfortably + up to 2 small children):br• Primary bedroom (2nd floor): Queen bed, vintage charm, TV, and storagebr• Second bedroom (2nd floor): Queen bed, calming natural light, TV, and storagebr• Full bathroom (2nd floor): Walk-in shower, located steps from both bedroomsbr• Third bedroom (1st floor): Train-themed bunk room with ensuite full bath — a playful nod to Madison’s railroad history. This 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 mattress providedbrbr 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• Dedicated game room — also rarebr• Walk-to-everything convenience reduces event-day parking chaosbr• Golf cart rental onsite (subject to availability)br• Historic charm paired with modern comfort upgradesbr• Excellent for Regatta, Chautauqua, Hanover College visits, and festivalsbr• Complimentary chocolate, snacks, and chilled sparkling waterbr• Room darkening curtains, ear plugs, & Dohm machine for restful sleepbrbr Family-Friendly Featuresbr• Highchair • Baby bath • Pack ’n Play • Toddler mattressbr• Game room with mini pool table, air hockey, ping pong, board games, and cardsbr• Tub in main-level bathroom off bunk roombr• Quiet neighborhood ideal for evening walksbrbr Outdoor Livingbr• Patio with pergola and café lightingbr• Hot tub and fire pit for shared outdoor relaxationbr• Gas grill with grilling toolsbr• Outdoor tables and seating for group meals or downtimebrbr 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.
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Sleep 8

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Exceptional(16)

$448.24

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Private Vacation Home

Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

Madison, Indiana, United States

Madison Manor II is a spacious historic townhouse just 2 blocks from the Ohio River, 5 blocks to the boat ramp, & a short walk to charming downtown Madison. One of the only homes in town with both a hot tub & game room, it sleeps up to 8 -- perfect for families & small groups.brbrEnjoy vintage character, modern comforts, a shared patio with hot tub, fire pit & grill, plus a mini-movie theater, dartboard, & more.brbrMadison Manor I adjoins Madison Manor II—book both homes together for larger groups. You may hear guests on the other side. Quiet hours are 10pm-8am. Earplugs and white noise machines are provided for your comfort & convenience.brbr✨ Highlightsbr• 2-story Townhouse • Private entry • See layout photobr• 2 bedrooms • 2.5 bathroomsbr• Sleeps 8 — 6 guests + 2 small childrenbr• 2 Queens · 2 Twin futons in game room (common area) · Toddler mattress · Pack-n-Play br• Ideal for families, groups, and couplesbr• Walk to Downtown Madison & the Ohio Riverbr• Free street parkingbr• Fully equipped kitchenbr• Ultra-fast WiFi • 3 Smart TVsbr• Washer & dryer in shared laundry roombr• Patio • Hot tub • Fire pit • Gas grill (shared amenities)br• Dedicated game room • Mini movie theater • Dartboard • Poker set • Board gamesbr• Golf cart rental (subject to availability)br• Adjoins Madison Manor I — book both townhouses & sleep up to 16br• Quiet, well-mannered dogs welcome with prior consent • Pet fee appliesbrbr— The Details —brThis Italianate-style townhouse built in 1870 offers a rare combination of prime location, architectural character, and standout amenities. Whether you’re visiting for a weekend getaway, a family trip, or an extended stay, Madison Manor II is designed for relaxation, connection, and memorable experiences. Inside, historic charm meets modern comfort with exposed brick and thoughtful décor. The well-equipped kitchen includes pantry basics and everything you need for easy meals at home.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.brbrSleeping arrangements (sleeps 6 comfortably + up to 2 infants):br• Primary bedroom (2nd floor): Queen four-poster bed with ivory bedspread, vintage charm, TV, and storagebr• Second bedroom (2nd floor): Queen bed with calming natural light, TV, and storagebr• Full bathroom (2nd floor): Located steps from both bedroomsbr• Living Room 2 / Game Room (1st floor): Two twin futonsbr• Second full bathroom (1st floor): Walk-in showerbr• Pack ’n Play and toddler mattress providedbrbrStep 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 areabrbr 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• Dedicated game room with mini movie theater — also rarebr• Walk-to-everything convenience reduces event-day parking chaosbr• Convenient onsite golf cart rental (subject to availability)br• Historic charm paired with modern comfort upgradesbr• Excellent for Regatta, Chautauqua, Hanover College visits, and festivalsbr• Complimentary chocolate, snacks, and chilled sparkling waterbr• Room darkening curtains, ear plugs, & Dohm machine for restful sleepbrbr Family-Friendly Featuresbr• Highchair • Baby bath • Pack ’n Play • Toddler mattressbr• Game room with mini movie theater, dartboard, poker set, board games, and cardsbr• Bathtub in upstairs bathroombr• Quiet neighborhood ideal for evening walksbrbr✨ Outdoor Livingbr• Patio with pergola and café lightingbr• Hot tub and fire pit for shared outdoor relaxationbr• Gas grill with grilling toolsbr• Outdoor tables and seating for group meals or downtimebrbr 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.
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$208.6

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Cabin

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Madison, Indiana, United States

Welcome to the Sonshine Cabin The cabin is located on approximately 15 acres and offers peace and quiet along with lots of wildlife to enjoy.. Conveniently located to Historic Madison ,Versailles, Friendship and 2 state parks. The cabin has 1800 sq of living space which includes a fully equipped , completely renovated kitchen to prepare meals. Enjoy your meals on a custom built table in the dining area. On the back deck you can enjoy grilling on a Blackstone grill with outdoor seating. On the main level is the great room with a stone fireplace. There is plenty of seating with a big leather sectional, a sleeper sofa to relax. Make your way up the stairs, you will notice the beautiful handmade cedar railings, made from cedar trees off the property. Upstairs you will find 3 private bedrooms all with Queen beds. We also have a toddler bed and provide a pack n play for smaller children. There is 1 full bath upstairs and a half bath on the main level. One of the favorite places is the front porch with seating to watch the wildlife! It is a short hike to the creek, which offers hours of fun for the kids. You can also enjoy roastingbrHotdogs and s’mores at the fire pit, pitch some horseshoes, or play some frisbee golf. If you are looking for a peaceful park like setting then Sonshine cabin is for you. We have recently added a security camera. It is on the outside of the cabin. There are no cameras inside the cabin. We respect your privacy and added the camera for security only. The cabin is located in a private area and we felt the camera would give guests additional peace of mind.
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$175.95

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Hotel

Midnight on Main Suite 203 at The Chandler Hotel

Madison, Indiana, United States

Summary:brbrLocated in the heart of Downtown Madison, The Chandler Hotel has a rich history while boasting sophistication and comfort for the modern traveler. This new, first-of-its kind boutique hotel gives a nod to the past while capturing a rich contemporary design featuring a rooftop terrace, fitness room, and spacious gathering areas. Each room is individually designed to offer a unique experience and pay homage to the charm and history of Madison.brbrbrbrThe Space:brbrEach room at The Chandler has been designed and curated to showcase the history and wonders of Madison.brbrbrbrThe heartbeat of small town America is Main Street. This iconic street in Downtown Madison is home to small business, unique shopping and delicious restaurants. Midnight on Main is a late night stroll; with inspiration from dark lampposts, softly lit shop windows, and vintage neons we give a nod to Downtown’s most beloved street. brbrbrbrThis boutique experience at the Midnight on Main Suite includes an oversized luxurious shower, local bath amenities, double vanity, mini-fridge, curated local coffee experience, SmartTV (complimentary Netflix), along with a king bed featuring premium bedding and luxe mattress.brbrbrbrGuest Access:brbrFeel more at home with our invisible service. The Chandler is equipped with modern and secure self check-in, allowing our guests to skip the front desk and head directly to their rooms or check out the best of Madison!brbrbrbrGuests are given one secure and individualized code upon booking. Your personal code will work for entry to The Chandler (front door), and your booked hotel room. brbrbrbrIn addition to your suite you will also have access to our lobby, rooftop terrace, and fitness room.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrThe Neighborhood:brbrThe Chandler Hotel is located in the heart of Downtown Madison, this premiere location is central to every festival and event. brbrbrbrLocated one block from Main Street which offers an array of diverse dining options and boutique shopping experiences, we are also two blocks from the beautiful Ohio River walk, and a 5 minute drive to Clifty Falls State Park. brbrbrbrExperience all that Madison has to offer when you stay at The Chandler Hotel.brbrbrbrGetting Around:brbrGolf cart friendly neighborhood (rentals available nearby), biking (rentals available nearby), walking or driving.brbrbrbrParking is street parking and public parking lots.brbrbrbrOther Things to Note:brbrMust be 21 years old with a valid photo ID to book and stay. brbrbrbrRegistered guests are permitted only.brbrbrbrCheck-in details including the access code are sent two days prior to arrival.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrPlease reference the digital manual sent via messaging for our local recommendations along with other helpful information.
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$175.95

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Hotel

The Stablemans Quarters 206 at The Chandler Hotel

Madison, Indiana, United States

Summary:brbrLocated in the heart of Downtown Madison, The Chandler Hotel has a rich history while boasting sophistication and comfort for the modern traveler. This new, first-of-its kind boutique hotel gives a nod to the past while capturing a rich contemporary design featuring a rooftop terrace, fitness room, and spacious gathering areas. Each room is individually designed to offer a unique experience and pay homage to the charm and history of Madison.brbrbrbrThe Space:brbrEach room at The Chandler has been designed and curated to showcase the history and wonders of Madison.brbrbrbrOriginally the building that is now The Chandler Hotel was a livery stable. Dating back to the 1870s up until the 1930s, Samuel Herin and Louis Eisenhardt were notable stablemasters and owners of the building. This suite preserves the fashion livery of the past including a headboard crafted from an original stable wall. Historic artifacts and photos from the time when these men owned the building can also be found in the hotel lobby. brbrbrbrThis boutique experience at The Stableman’s Quarters Suite includes an oversized luxurious shower, local bath amenities, double vanity, mini-fridge, curated local coffee experience, SmartTV (complimentary Netflix), along with a king bed featuring premium bedding and luxe mattress.brbrbrbrGuest Access:brbrFeel more at home with our invisible service. The Chandler is equipped with modern and secure self check-in, allowing our guests to skip the front desk and head directly to their rooms or check out the best of Madison!brbrbrbrGuests are given one secure and individualized code upon booking. Your personal code will work for entry to The Chandler (front door), and your booked hotel room. brbrbrbrIn addition to your suite you will also have access to our lobby, rooftop terrace, and fitness room.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbr*Codes are only active for the duration of your stay and will automatically expire. Registered guests only are permitted*brbrbrbrThe Neighborhood:brbrThe Chandler Hotel is located in the heart of Downtown Madison, this premiere location is central to every festival and event.brbrbrbrLocated one block from Main Street which offers an array of diverse dining options and boutique shopping experiences, we are also two blocks from the beautiful Ohio River walk, and a 5 minute drive to Clifty Falls State Park.brbrbrbrExperience all that Madison has to offer when you stay at The Chandler Hotel.brbrbrbrGetting Around:brbrGolf cart friendly neighborhood (rentals available nearby), biking (rentals available nearby), walking or driving.brbrbrbrParking is street parking and public parking lots.brbrbrbrOther Things to Note:brbrMust be 21 years old with a valid photo ID to book and stay. brbrbrbrRegistered guests are permitted only.brbrbrbrCheck-in details including the access code are sent two days prior to arrival.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrPlease reference the digital manual sent via messaging for our local recommendations along with other helpful information.
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$175.95

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Hotel

La Belle Rivière Suite 202 at The Chandler Hotel

Madison, Indiana, United States

Summary:brbrLocated in the heart of Downtown Madison, The Chandler Hotel has a rich history while boasting sophistication and comfort for the modern traveler. This new, first-of-its kind boutique hotel gives a nod to the past while capturing a rich contemporary design featuring a rooftop terrace, fitness room, and spacious gathering areas. Each room is individually designed to offer a unique experience and pay homage to the charm and history of Madison.brbrbrbrThe Space:brbrEach room at The Chandler has been designed and curated to showcase the history and wonders of Madison.brbrbrbrThe majestic rivertown of Madison wouldn’t exist without The Mighty Ohio. One of the first Europeans to see the Ohio River was Frenchman Rene Robert Cavelier, Sieur de La Salle in 1669. He named the river la belle rivière or the beautiful river. From steamboats of the past to today’s hydroplane races at the Madison Regatta, the Ohio River continues to be a main attraction of Historic Downtown Madison - The La Belle Rivière Suite pays homage to this natural wonder.brbrbrbrThis boutique experience at the La Belle Rivière Suite includes an oversized luxurious shower, local bath amenities, double vanity, mini-fridge, curated local coffee experience, SmartTV (complimentary Netflix), along with two queen beds premium bedding and luxe mattresses.brbrbrbrGuest Access:brbrFeel more at home with our invisible service. The Chandler is equipped with modern and secure access, allowing our guests to skip the front desk and head directly to their rooms or check out the best of Madison!brbrbrbrGuests are given one secure and individualized code upon booking. Your personal code will work for entry to The Chandler (front door), and your booked hotel room. brbrbrbrIn addition to your suite you will also have access to our lobby, rooftop patio, and fitness area.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbr*Codes are only active for the duration of your stay and will automatically expire. Registered guests only are permitted*brbrbrbrThe Neighborhood:brbrThe Chandler Hotel is located in the heart of Downtown Madison, this premiere location is central to every festival and event. brbrbrbrLocated one block from Main Street which offers an array of diverse dining options and boutique shopping experiences, we are also two blocks from the beautiful Ohio River walk, and a 5 minute drive to Clifty Falls State Park. brbrbrbrExperience all that Madison has to offer when you stay at The Chandler Hotel.brbrbrbrGetting Around:brbrGolf cart friendly neighborhood (rentals available nearby), biking (rentals available nearby), walking or driving.brbrbrbrParking is street parking and public parking lots.brbrbrbrOther Things to Note:brbrMust be 21 years old with a valid photo ID to book and stay. brbrbrbrRegistered guests are permitted only.brbrbrbrCheck-in details including the access code are sent two days prior to arrival.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrPlease reference the digital manual sent via messaging for our local recommendations along with other helpful information.
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Exceptional(5)

$175.95

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Hotel

The Lanier Suite 204 at The Chandler Hotel

Madison, Indiana, United States

Summary:brbrLocated in the heart of Downtown Madison, The Chandler Hotel has a rich history while boasting sophistication and comfort for the modern traveler. This new, first-of-its kind boutique hotel gives a nod to the past while capturing a rich contemporary design featuring a rooftop terrace, fitness room, and spacious gathering areas. Each room is individually designed to offer a unique experience and pay homage to the charm and history of Madison.brbrbrbrThe Space:brbrEach room at The Chandler has been designed and curated to showcase the history and wonders of Madison.brbrbrbrJames Lanier was an entrepreneur who lived in Madison during the 1800s. Lanier was a wealthy banker with strong interest in real estate and railroads. He is more famously known for loaning the Indiana government over one million dollars without security to help the state avoid bankruptcy during the American Civil War. The Lanier Mansion is a staple landmark of Madison; The Lanier Suite honors Lanier’s legacy and puts a modern twist on “The Informal Parlor” in Lanier’s mansion with inspiration from the deep green drapes and gold accents from the historic wallpaper.brbrbrbrThis boutique experience at The Lanier Suite includes an oversized luxurious shower, local bath amenities, double vanity, mini-fridge, curated local coffee experience, SmartTV (complimentary Netflix), along with a king bed featuring premium bedding and luxe mattress.brbrbrbrGuest Access:brbrFeel more at home with our invisible service. The Chandler is equipped with modern and secure self check-in, allowing our guests to skip the front desk and head directly to their rooms or check out the best of Madison!brbrbrbrGuests are given one secure and individualized code upon booking. Your personal code will work for entry to The Chandler (front door), and your booked hotel room. brbrbrbrIn addition to your suite you will also have access to our lobby, rooftop terrace, and fitness room.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbr*Codes are only active for the duration of your stay and will automatically expire. Registered guests only are permitted*brbrbrbrThe Neighborhood:brbrThe Chandler Hotel is located in the heart of Downtown Madison, this premiere location is central to every festival and event.brbrbrbrLocated one block from Main Street which offers an array of diverse dining options and boutique shopping experiences, we are also two blocks from the beautiful Ohio River walk, and a 5 minute drive to Clifty Falls State Park.brbrbrbrExperience all that Madison has to offer when you stay at The Chandler Hotel.brbrbrbrGetting Around:brbrGolf cart friendly neighborhood (rentals available nearby), biking (rentals available nearby), walking or driving.brbrbrbrParking is street parking and public parking lots.brbrbrbrOther Things to Note:brbrMust be 21 years old with a valid photo ID to book and stay. brbrbrbrRegistered guests are permitted only.brbrbrbrCheck-in details including the access code are sent two days prior to arrival.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrPlease reference the digital manual sent via messaging for our local recommendations along with other helpful information.
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$175.95

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Hotel

Sunset on Broadway Suite 205 at The Chandler Hotel

Madison, Indiana, United States

Summary:brbrLocated in the heart of Downtown Madison, The Chandler Hotel has a rich history while boasting sophistication and comfort for the modern traveler. This new, first-of-its kind boutique hotel gives a nod to the past while capturing a rich contemporary design featuring a rooftop terrace, fitness room, and spacious gathering areas. Each room is individually designed to offer a unique experience and pay homage to the charm and history of Madison.brbrbrbrThe Space:brbrEach room at The Chandler has been designed and curated to showcase the history and wonders of Madison.brbrbrbrThe Broadway Fountain, a Madison treasure, is a bronze copy of the original nineteenth-century iron fountain that was part of the Philadelphia Centennial Exposition of 1876. Sunset on Broadway highlights deep hues of burgundy, accented with gold and autumn orange tones, celebrating this architectural wonder. During your visit be sure not to miss a sunset on Broadway.brbrbrbrThis boutique experience at the Sunset on Broadway suite includes an oversized luxurious shower, local bath amenities, double vanity, mini-fridge, curated local coffee experience, SmartTV (complimentary Netflix), along with a king bed featuring premium bedding and luxe mattress.brbrbrbrGuest Access:brbrFeel more at home with our invisible service. The Chandler is equipped with modern and secure self check-in, allowing our guests to skip the front desk and head directly to their rooms or check out the best of Madison!brbrbrbrGuests are given one secure and individualized code upon booking. Your personal code will work for entry to The Chandler (front door), and your booked hotel room. brbrbrbrIn addition to your suite you will also have access to our lobby, rooftop terrace, and fitness room.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbr*Codes are only active for the duration of your stay and will automatically expire. Registered guests only are permitted*brbrbrbrThe Neighborhood:brbrThe Chandler Hotel is located in the heart of Downtown Madison, this premiere location is central to every festival and event. brbrbrbrLocated one block from Main Street which offers an array of diverse dining options and boutique shopping experiences, we are also two blocks from the beautiful Ohio River walk, and a 5 minute drive to Clifty Falls State Park. brbrbrbrExperience all that Madison has to offer when you stay at The Chandler Hotel.brbrbrbrGetting Around:brbrGolf cart friendly neighborhood (rentals available nearby), biking (rentals available nearby), walking or driving.brbrbrbrParking is street parking and public parking lots.brbrbrbrOther Things to Note:brbrMust be 21 years old with a valid photo ID to book and stay. brbrbrbrRegistered guests are permitted only.brbrbrbrCheck-in details including the access code are sent two days prior to arrival.brbrbrbrThe hotel does not contain an elevator, guests who book on the second floor must be able to climb stairs. Please note that when booking a suite, suites room numbers that start with 1 are located on the first floor, suite numbers that start with 2 are located on the second floor.brbrbrbrPlease reference the digital manual sent via messaging for our local recommendations along with other helpful information.
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Home Most popular vacation rentals in Madison