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Entire home

The Winston on Market - Private Luxury Rental Space

Holiday home with kitchen, a short walk to Fourth Street Live!

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

Interior
Fridge, microwave, oven, stovetop
Interior
2 bedrooms, iron/ironing board, WiFi, bed sheets
Lobby
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 NZ$961
includes taxes & fees
13 Oct - 14 Oct

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 house: WiFi

Parking and transport

  • Parking on site

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

  • 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)

General

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

Similar properties

Outdoor dining

Side-by-side King Bed Suites!

  • Kitchen
  • Washer
  • Air conditioning
  • Parking available
10.0 out of 10, Exceptional, 1 review
The price is NZ$1,263
includes taxes & fees
17 Oct - 18 Oct
Side-by-side King Bed Suites!

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

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

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
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

Downtown Louisville, a neighbourhood in Louisville, is home to this holiday home. Louisville Slugger Museum and KFC Yum Center are cultural highlights, and some of the area's popular attractions include Kentucky Kingdom and Louisville Zoo. Looking to enjoy an event or a game? See what's going on at Churchill Downs or L&N Federal Credit Union Stadium.
Visit our Louisville travel guideOpens in a new window
View more Condo rentals in LouisvilleOpens in a new window
Map
Louisville, KY

What's nearby

  • Louisville Slugger Museum - 5 min walk - 0.4 km
  • Fourth Street Live! - 6 min walk - 0.6 km
  • Kentucky International Convention Center - 6 min walk - 0.6 km
  • KFC Yum Center - 8 min walk - 0.7 km
  • Whiskey Row - 8 min walk - 0.7 km

Getting around

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

Restaurants

  • ‪Heine Brothers' Coffee - ‬2 min walk
  • ‪Mussel & Burger Bar - ‬3 min walk
  • ‪Bristol Bar and Grille - ‬2 min walk
  • ‪Vincenzo's Italian Restaurant - ‬2 min walk
  • ‪Pokehana - ‬2 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 4 Oct 2025, prices found for a 1-night stay for 2 adults at The Winston on Market - Private Luxury Rental Space on 13 Oct 2025 start from NZ$961.47, 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.

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 holiday home is within a 10-minute walk of Evan Williams Bourbon Experience, Fourth Street Live! and Louisville Slugger Museum. KFC Yum Center and Whiskey Row are also within 10 minutes.

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