10/10 Excellent
Tom F.
3 Dec 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tom F.
Stayed 2 nights in Nov 2025
Entire home
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
Holiday home in Madison with kitchen and patio
Photo gallery for Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
Reviews
10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6295.0 sq m
Popular amenities
Explore the area
Madison, IN
- Place, Lanier Mansion2 min walk
- Place, Schofield House5 min walk
- Place, Historic District6 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.
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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9.6 out of 10, Exceptional, (24 reviews)
House Rules
Check in after 2:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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
We should mention
This property does not have any lifts
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.
Madison, IN
What's nearby
- Lanier Mansion - 2 min walk - 0.2 km
- Madison Railroad Station Museum - 3 min walk - 0.3 km
- Lanthier Winery - 5 min walk - 0.4 km
- Schofield House - 5 min walk - 0.4 km
- Historic District - 6 min walk - 0.6 km
Getting around
Restaurants
- Dairy Queen - 3 min drive
- The Red Pepperoni - 11 min walk
- Moose Lodge - 3 min drive
- Vintage Lanes Wine Bar - 11 min walk
- Madison Lighthouse Restaurant - 9 min walk
Frequently asked questions
Reviews
10
Exceptional
10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Lee M.
16 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lee M.
Stayed 3 nights in Oct 2025
About the host
Hosted by Miles Lowenfield
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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