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Entire condo·Private host

The Winston on Market - Private Luxury Rental Space

Condo with kitchen, 6-minute walk to Louisville Slugger Museum

Photo gallery for The Winston on Market - Private Luxury Rental Space

Interior - The Winston on Market - Private Luxury Rental Space (Louisville)
Interior - The Winston on Market - Private Luxury Rental Space (Louisville)
Lobby - The Winston on Market - Private Luxury Rental Space (Louisville)
Fridge, microwave, oven, stovetop - The Winston on Market - Private Luxury Rental Space (Louisville)
Interior - The Winston on Market - Private Luxury Rental Space (Louisville)
Close to Kentucky International Convention Center and Louisville Slugger Museum, The Winston on Market - Private Luxury Rental Space provides amenities such as laundry facilities. Treat yourself to a massage or other spa services. Guests can connect to in-room WiFi.

Entire condo

2 bedrooms1 bathroom186 sq m

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Kitchen
  • Parking available
  • Air conditioning
The current price is €466
includes taxes & fees
11 Jan - 12 Jan 2026

Add dates for prices

About this property

Entire place

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

The Winston on Market - Private Luxury Rental Space

Welcome to The Winston on Market – A "Private" Short-Term & Event Rental Space

Nestled in the heart of downtown Louisville, KY, located inside The Old Portland Building at 539 W. Market St. offers a one-of-a-kind stay and event experience in a historic setting. Built in 1882, this beautifully restored gem blends timeless charm with modern comforts, making it the perfect destination for travelers, special occasions, and corporate gatherings.

Stay in History!

Our thoughtfully designed accommodations provide guests with a cozy yet stylish retreat, featuring elegant décor, modern amenities, and a rich sense of history. Whether you're visiting Louisville for a weekend getaway, business trip, or a local event, The Old Portland Building offers a memorable stay in a prime location.

Host Your Next Event!

With its classic architecture, spacious layout, and warm ambiance, The Old Portland Building is an ideal venue for weddings, receptions, private parties, corporate meetings, and other special gatherings. Our flexible rental space can be tailored to suit your event's needs, creating a truly unique and unforgettable experience.

Why Choose The Winston on Market?

✔ Historic Charm – Experience the character and elegance of a 19th-century landmark.
✔ Prime Location – Conveniently situated in downtown Louisville, close to top attractions, dining, and entertainment.
✔ Versatile Event Space – Perfect for intimate celebrations, corporate functions, and more.
✔ Comfort & Convenience – Enjoy modern amenities in a beautifully preserved historic setting.
✔ Complete Privacy – There is private elevator access and on the weekends (F-Sun) the main entrance can be locked for additional security/privacy
✔ Convenient Parking – There is on the street parking, an adjacent parking lot and two parking garages (all pay to park options).

Discover the charm of The Winston on Market located inside the Old Portland Building – where history meets modern luxury. Book your stay or event with us today!

Amenities Include:
- Approx 1,900 sqft (Holds up to 64-75 people)
- Two Bedrooms
- Full Kitchen
- Onsite Laundry
- Marble style flooring
- Full body length LED smart mirror
- Bidet Smart Toilet
- 15' Celinings
- Panoramic view of the city
- 10' windows
- Private Elevator Access
- AV Sound System

Customize your stay with Oniste
- Personal Chef Services
- Mobile Massage Therapy Services
- Make-up Artist
- Other services by request
* Contact us for pricing

Pricing
- Overnight Stay - $1000 / Night
- Event - $1000 / 6 hours
- Special Event (Includes overnight stay) - $2000 / Night
- Contact us for pricing during holidays and local events

***BOOK TODAY - This place typically sells out fast!

*Prices vary depending on holidays and local event*

Property amenities

Pool/Spa

  • Massage

Internet

  • Available in the condo: WiFi

Parking and transport

  • Wheelchair-accessible parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator

Dining

  • Chef service

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bidet
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • Smart TV

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.
  • Accessible parking space
  • Lift
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

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

General

  • At least 80% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Recycling
  • Unit size: 2,000 square feet
  • Water-efficient toilets

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Policies

Check-in

Check-in time starts at 2:00 PM
Minimum check-in age - 25

Check-out

Check-out before 12:00 PM

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

Rules

Sub renting/leasing not allowed. Individuals are not permitted to rent on behalf of another person.
Violations of any policy can result in the immediate termination of the agreement and renters will be asked to vacate the premises.
Strict noise policy enforced Monday-Friday 8a-5p.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings, birthday parties, weddings
Contact us for event rental pricing and terms

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 65
Note from host: Contact us for event rental pricing and terms
Long-term renters welcome
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
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
Property Registration Number LIC-STL-25-00250

About the area

Map
Louisville, KY

What's nearby

  • 21c Museum Hotel - 2 min walk - 0.2 km
  • Muhammad Ali Center - 3 min walk - 0.3 km
  • Louisville Slugger Museum - 5 min walk - 0.4 km
  • Kentucky International Convention Center - 6 min walk - 0.6 km
  • KFC Yum Center - 8 min walk - 0.7 km

Getting around

  • Louisville, KY (LOU-Bowman Field) - 15 min drive

Restaurants

  • ‪Heine Brothers' Coffee - ‬2 min walk
  • ‪Vincenzo's Italian Restaurant - ‬2 min walk
  • ‪Mussel & Burger Bar - ‬3 min walk
  • ‪Sunergos Coffee and Espresso Bar - ‬3 min walk
  • ‪Proof on Main - ‬3 min walk

Frequently asked questions

Is The Winston on Market - Private Luxury Rental Space pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Winston on Market - Private Luxury Rental Space?

As of 17 Dec 2025, prices found for a 1-night stay for 2 adults at The Winston on Market - Private Luxury Rental Space on 11 Jan 2026 start from €466.11, 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 The Winston on Market - Private Luxury Rental Space?

On-site parking is available at the property.

What time is check-in at The Winston on Market - Private Luxury Rental Space?

Check-in begins at 2:00 PM.

What time is check-out at The Winston on Market - Private Luxury Rental Space?

Checkout is at 12:00 PM.

Where is The Winston on Market - Private Luxury Rental Space located?

Located in Downtown Louisville, this condo building is within a 10-minute walk of Ohio River Valley, Louisville Slugger Museum and KFC Yum Center. Evan Williams Bourbon Experience and Kentucky Center for the Performing Arts are just steps away.

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