Entire home

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

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

A front door with the number 505, a blue door, and two potted plants on either side.
A fireplace with a white mantel and a large mirror above it.
A kitchen with white cabinetry, a stainless steel refrigerator, granite countertops, and a window with a blue valance.
A dining area with a wooden table and chairs, a staircase with a railing, and a living room with a sofa and a coffee table.
A staircase with wooden balusters and a black handrail leading to an upper floor.

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Near Ohio River Valley

Popular amenities

  • Patio
  • Air conditioning
  • Internet
  • Washer
  • Onsite parking available
  • Microwave

Explore the area

View in a map
Madison, IN
  • Place, Lanier Mansion
    ‪2 min walk‬
  • Place, Schofield House
    ‪5 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 Twin 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

Add dates for prices

Similar properties

Upscale decor invites you into this perfect getaway!
Livery Loft: our other BEST downtown location! Award winning! Come see why.
Madison Historic District
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
10.0 out of 10, Exceptional, (28 reviews)
Livery Loft: our other BEST downtown location! Award winning! Come see why.

About the neighborhood

Madison

Located in Madison, this vacation home is in the city center. 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 Vacation 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 Intl. Airport (SDF) - 66 min drive

Restaurants

  • ‪Dairy Queen - ‬3 min drive
  • ‪Taco Bell - ‬6 min drive
  • ‪Circle K - ‬5 min drive
  • ‪Circle K - ‬11 min walk
  • ‪Boneyard Grill - ‬5 min drive

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 Oct 31, 2026, prices found for a 1-night stay for 2 adults at Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront on Jan 3, 2027 start from $383, 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?

Onsite 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?

Check-out is at 10:00 AM.

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

Located in Madison Historic District, this vacation home is steps 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 labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 12 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was beautiful and very clean. We enjoyed our visit to the town. The house is in a perfect location.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect home rental for a downtown Madison stay. Spacious rooms with great common areas. A fully stocked kitchen, dining room and a nice outdoor area with lights at the end of the day. The home is ideally situated to walk the riverfront and visit shops, restaurants and the downtown Madison area. We will absolutely stay here again when we come back to Madison!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, spacious and clean. Easy check in. Check out was at 10, a little early for us, but they did have an early 2:00 check in. The host had sound machines and charging stations in all the bedrooms. Very comfortable beds and bedding. Thermostat on both floors. We had a great stay. would definitely stay again.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was very enjoyable. We loved the comfortable beds, the beautiful well furnished kitchen, and the lovely decor and furnishings with several places to sit and relax. The hosts are quick to respond with any questions/needs. We were interested in the history of this 1846 building and hope to return one day to get the full story! (Do note there are some long stairs up to the bedrooms when deciding about staying here.) Very conveniently located with walking an option to the river and shops along Main. Thanks for a fun and comfortable stay!
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house and amenities were fantastic. Beds were very comfortable! This was a sisters trip and everyone enjoyed the space and we had a great time catching up and exploring Madison! The host was wonderful!
Stayed 2 nights in Apr 2026
Response from VrboOwner on Apr 28, 2026
We are so happy to hear that you had a good sisters trip in Madison! Historic Main Street has so much to offer and we are grateful you chose us! Come again!
Verified review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is exceptional; even more amazing than what was described! Communication was timely and thorough for check-in/out process. The hosts thought of everything: toiletries you might’ve forgotten at home, several game options if your family chose a night in, cozy throw blankets, cold water in the refrigerator upon your arrival, even umbrellas for your personal use in the event your vacation ends up being soggy, rainy, and sometimes stormy. The house was immaculately clean, the location was perfection for walking around downtown and enjoying all the town has to offer, and I would definitely recommend this property for anyone vacationing in or near Madison, IN.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, beautiful, very clean. Walkable to coffee, lunch, and dinner location. Parking close to house. Would highly recommend to friends. Wish we could have stayed longer!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, comfy and spacious historical house that is modernized where it counts. It was great to walk to shops and restaurants. It was a girls trip and we loved our stay!
Stayed 3 nights in Jun 2026
Response from VrboOwner on Jun 26, 2026
Thank you so much for your wonderful review, Deb! We’re delighted to hear your group enjoyed the comfort, space, and historic charm of the home, along with its convenient walkable location. It was a pleasure hosting your girls’ trip, and we’d love to welcome you back anytime you’re in Madison. Thank you again for choosing Sycamore Hollow On Main!
Verified review

10/10 Excellent

Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Stayed 2 nights in Jun 2026
Tell us how we can improve our siteShare feedback