The Winston on Market - Private Luxury Rental Space | Condo in Louisville
2 Bedroom Condo in West Main Historic District, Louisville
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*
The Winston on Market - Private Luxury Rental Space is located in West Main Historic District. The Winston on Market - Private Luxury Rental Space provides accommodation, featuring Air Conditioner, Parking, Bedding/Linens, among other amenities. This Condo features Air Conditioner, Parking, Bedding/Linens, to make your stay a comfortable one.
The Winston on Market - Private Luxury Rental Space has 2 Bedrooms , 1 Bathroom, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Condo because of the excellent services rendered by the owner or manager of this Condo, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Condo has a friendly neighborhood, and the West Main Historic District has interesting places to visit. If you want to learn more about the Condo in West Main Historic District, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
-
Air conditioning
-
Heating
-
Toilet paper
-
Shower
-
Bidet
-
Soap
-
Towels provided
-
1 bathroom
-
2 bedrooms
-
Bed sheets provided
-
Fireplace
-
Cookware/dishes/utensils
-
Ice maker
-
Dishwasher
-
Coffee/tea maker
-
Microwave
-
Refrigerator
-
Stovetop
-
Oven
-
Laundry facilities
-
Washing machine and dryer
-
Onsite parking
-
No pets allowed
-
Smoke-free property
-
Smart TV
-
At least 80% lighting from LEDs
-
Recycling
-
Energy-saving switches
-
Water-efficient toilets only
-
Unit size: 2000 sq ft (186 sq m)
-
English
-
Iron/ironing board
-
Chef
-
WiFi available
-
Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
-
Smoke detector installed (host has indicated there is a smoke detector on the property)
-
Massages
Policies
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property long-term renters welcome note from host: contact us for event rental pricing and terms parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 65 property registration number lic-stl-25-00250 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
