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Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio

Vacation home perfectly located for exploring Madison

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A modern kitchen with a large island, wooden cabinets, and stainless steel appliances.
A modern living room with large windows, a fireplace, and a flat-screen TV.
A cozy seating area with a sofa, cushions, a potted plant, and a wooden coffee table.
A row of brick buildings with storefronts, a sidewalk, and a tree.
48 web or mls SAV09350

Entire home

1 bedroom1 bathroom1056 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Madison, IN
  • Place, Historic District
    ‪3 min walk‬
  • Place, Schofield House
    ‪5 min walk‬
  • Place, Lanier Mansion
    ‪9 min walk‬

Room options

About the neighborhood

Madison

Heart of Madison.A stay at this Madison Historic District vacation home places you steps from Thomas Family Winery and within a 5-minute walk of Ohio River Valley. Historic District and Dr. William Hutching's Office & Hosptal are also within half a mile (1 km).
View more Vacation Homes in MadisonOpens in a new window

What's nearby

  • Historic District - 3 min walk - 0.2 miles
  • Schofield House - 5 min walk - 0.3 miles
  • Jeremiah Sullivan House - 6 min walk - 0.4 miles
  • Lanier Mansion - 9 min walk - 0.5 miles
  • Madison Railroad Station Museum - 11 min walk - 0.6 miles

Getting around

  • Louisville Intl. Airport (SDF) - 73 min drive

Restaurants

  • ‪Dairy Queen - ‬2 min drive
  • ‪Taco Bell - ‬5 min drive
  • ‪Circle K - ‬5 min drive
  • ‪Circle K - ‬3 min walk
  • ‪Boneyard Grill - ‬6 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio

Settle into a piece of Madison’s history at Rooftop on Main. This 1840s building has been thoughtfully restored as a welcoming downtown retreat, bringing historic character together with the modern comforts guests appreciate. For the holiday season, we’re adding festive touches each week to create a warm, memorable Christmas getaway.

Enjoy a private rooftop patio, a custom arched walk-in shower, double vanity, and a full kitchen with quartz countertops. The queen bedroom and living room sleeper sofa accommodate up to four guests. Step outside and you’re within walking distance of Main Street restaurants, shops, bars, and local attractions.

Whether you’re planning a couple’s escape, a weekend away, or a special occasion, Rooftop on Main offers a comfortable home base in the heart of historic Madison.

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An outdoor patio with a hot tub, a fire pit, and string lights.
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  • Hot tub
  • Kitchen
  • Washer
  • Dryer
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Nov 17 - Nov 18
Total with taxes and fees
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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • No onsite parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop

Bedrooms

  • 1 bedroom
  • Bed sheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Smart TV

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator
  • Stair-free path to entrance
  • Smoking not allowed

Location highlights

  • In the city center
  • Near a hospital
  • Near a river

Things to do

  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking nearby
  • Motor boating nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit

General

  • Living plant wall
  • Some LED lighting used
  • Unit size: 1,056 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. No onsite parking is available. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

839157

Frequently asked questions

How close is Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio to the airport?

This vacation home is 53.8 mi (73-min drive) away from the Louisville Intl. Airport (SDF) airport, the closest popular airport to the property.

How much does it cost to stay at Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio?

As of Nov 6, 2026, prices found for a 1-night stay for 2 adults at Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio on Nov 10, 2026 start from $274, 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.

Does Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio?

No, there is no casino at this vacation home.

What time is check-in at Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio?

Check-in begins at 4:00 PM.

Is there free parking at Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio?

Free parking is not available at this vacation home.

Does Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio have a pool?

This vacation home does not have a pool.

Does Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio have a spa?

There are no spa services available at this vacation home.

How close is Rooftop on Main- Luxury Downtown Stay with Private Rooftop Patio to downtown Madison?

This vacation home is 0.1 mi away from Madison.

Christmas on Main! Luxury Stay above Main Street-Private Rooftop Patio Reviews