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

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

Interior
Exterior detail
Interior
Outdoor dining
Living area

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 63175 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View in a map
Madison, IN
  • Place, Lanier Mansion
    ‪2 min walk‬
  • Place, Madison Railroad Station Museum
    ‪3 min walk‬
  • Place, Historic District
    ‪6 min walk‬

Rooms & beds

3 bedrooms (sleeps 6)

Master Bedroom

1 King Bed

Queen Room

1 Queen Bed

Twin Room

2 Single Beds

2 bathrooms, 1 half bathroom

Master Bathroom

Soap · Towels provided · Toilet · Shower only · Jetted bathtub · Shampoo · Hair dryer

Powder Room

Soap · Towels provided · Toilet

Queen Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen

About this property

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

505 W Main Street – Historic Downtown Madison, Indiana

Sleeps 6 | 3 Bedrooms | 2.5 Baths | High-Speed Wi-Fi | Walk to Riverfront & Shops

Relax 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.

The Space
• Bedrooms (Sleeps 6)
Primary Suite: 1 King bed
Bedroom 2: 1 Queen bed
Bedroom 3: 2 Twin beds
• Bathrooms
2 full baths (both with showers) plus 1 half bath for convenience.
• Living & Dining
Bright, 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.
• Kitchen
Fully stocked for real cooking—full-size appliances, cookware, and all basic kitchen utilities.
• Laundry
Washer and dryer with detergent provided.
• Comfort Features
Central heating and cooling, ceiling fans in key rooms, and high-speed Wi-Fi for work or play.

⸻

Outdoor Living

Relax in the backyard patio and covered seating area, perfect for morning coffee or evening conversations.

⸻

Family-Friendly Touches

Pack ’n play, high chair, plus games and books make family travel easier and more fun.

⸻

Parking & Access
• Street Parking: Usually at least one space directly on Main Street in front of the home; additional parking on Elm Street just steps away.
• Smart Lock Check-In: Secure, contactless entry with your unique code.
• Check-in: 2:00 PM | Check-out: 10:00 AM

⸻

Location Highlights

Set right on Main Street in Madison’s celebrated Historic District:
• Ohio Riverfront Walk and Lanier Mansion are just a short stroll away.
• Boutique shopping, cafés, and local restaurants line the surrounding blocks.
• Quick 5-10 minute drive to Clifty Falls State Park with waterfalls and hiking trails.

⸻

House Rules
• No pets
• No smoking, candles, or events
• Quiet hours 9 PM – 8 AM to ensure a peaceful stay for everyone.

⸻

Why Guests Love 505 W Main
• Prime downtown location—park once and explore on foot
• Fresh, elegant furnishings and beds throughout
• Thoughtful extras for families and long-weekend getaways

Come experience the best of Madison, Indiana—where historic charm and modern comfort meet at 505 W Main Street.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Parking available

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House Rules

Check in after 2:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Madison

Located in Madison, this holiday home is in the city centre. Lanier Mansion and Francis Costigan House are cultural highlights, and some of the area's activities can be experienced at Lanthier Winery and Thomas Family Winery.
View more Holiday homes in MadisonOpens in a new window
Map
Madison, IN

What's nearby

  • Lanier Mansion - 2 min walk - 0.2 km
  • Madison Railroad Station Museum - 3 min walk - 0.3 km
  • Jeremiah Sullivan House - 3 min walk - 0.3 km
  • Schofield House - 5 min walk - 0.4 km
  • Historic District - 6 min walk - 0.6 km

Getting around

  • Louisville International Airport (SDF) - 66 min drive

Restaurants

  • ‪Dairy Queen - ‬3 min drive
  • ‪Moose Lodge - ‬3 min drive
  • ‪The Red Pepperoni - ‬11 min walk
  • ‪Subway - ‬5 min drive
  • ‪Vintage Lanes Wine Bar - ‬11 min walk

Frequently asked questions

Is Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront?

As of 3 Apr, 2026, prices found for a 1-night stay for 2 adults at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront on 7 Jul, 2026 start from S$445, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront?

On-site parking is available at the property.

What time is check-in at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront?

Check-in begins at 2:00 PM.

What time is check-out at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront?

Checkout is at 10:00 AM.

Where is Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront located?

Located in the heart of Madison, this holiday home is steps away from Ohio River Valley, Broadway Fountain and Lanier Mansion. Francis Costigan House and Madison Railroad Station Museum are just steps away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Tom F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cleanliness and high-quality items!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Lee M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay at this beautiful old home on Main Street in Madison was fantastic. The property has been beautifully maintained and modernized just enough to be comfortable without losing the gorgeous, authentic feel of an old home that clearly has stories to tell.The rooms were spacious and incredibly comfortable, providing plenty of room to relax. The location simply can't be beat—we loved that we could easily walk to all the local shops and great restaurants.Finally, the hosts were wonderfully helpful and provided a perfectly smooth, hands-off experience. We appreciated that they don't live on-site, which truly made the house feel like our own private retreat. We highly recommend this property!
Upstairs. There are 2 sets of stairways.
Main bedroom. Comfy.
Large main bathroom with tub and shower.
Modern kitchen
Stayed 3 nights in Oct 2025

About the host

Hosted by Miles Lowenfield

Host profile image
We’re Miles and Regina Lowenfield, a husband-and-wife team who love creating welcoming spaces for families and friends to relax and connect. Together with our three children, we enjoy caring for our farm and retreat property nearby and making sure our guests feel truly at home. Hosting lets us share our heart for hospitality—providing a place that is peaceful, thoughtfully prepared, and ready for lasting memories.

Why they chose this property

Downtown Madison blends historic charm with easy access to shops, cafés, and the Ohio River. We were drawn to the quiet, tree-lined Main Street setting and the ability to stroll to local restaurants, antique stores, and seasonal festivals. It offers the best of both worlds: a calm residential feel with plenty to explore just steps away.

What makes this property unique

505 W Main Street combines classic character with modern comfort. The home is freshly furnished with high-quality beds and cozy living spaces, equipped with fast Wi-Fi, two smart TVs, and a fully stocked kitchen. Families especially appreciate the kid-friendly touches—games, books, high chair, and pack ’n play—plus a private backyard patio and covered seating area that make it easy to unwind after a day in town.
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