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 Parking, Security/Safety, Bedding/Linens, among other amenities. This Condo features Parking, Security/Safety, 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
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Air conditioning
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Heating
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Shower
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Towels provided
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Toilet paper
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Soap
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1 bathroom
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Bidet
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Bed sheets provided
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2 bedrooms
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Fireplace
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Microwave
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Refrigerator
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Cookware/dishes/utensils
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Dishwasher
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Coffee/tea maker
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Stovetop
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Oven
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Ice maker
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Laundry facilities
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Washing machine and dryer
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Onsite parking
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No pets allowed
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Smoke-free property
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Smart TV
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Unit size: 2000 sq ft (186 sq m)
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At least 80% lighting from LEDs
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Water-efficient toilets only
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Recycling
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Energy-saving switches
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English
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Chef
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Iron/ironing board
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WiFi available
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Massages
Policies
FAQ's
Is this West Main Historic District condo pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the West Main Historic District condo have a swimming pool?
No, this West Main Historic District condo does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in West Main Historic District condo?
Best-rates for the West Main Historic District condo starts from $515 per night with includes Bedding/Linens, Fireplace/Heating, Child Friendly, Laundry, Air Conditioner, TV, Internet, Kitchen, Parking, Security/Safety At SunSki Resorts, we pair every traveler with their perfect accommodation, complete with all necessary facilities. Whether you're traveling with a group, friends, family, or pets, we have the ideal rental for you.
Is West Main Historic District condo a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this condo Good or guests have recommended them suitable for families. As reported by the owner or manager, the condo has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the West Main Historic District condo wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the West Main Historic District condo has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the West Main Historic District condo?
Based on the information reported by the owner or manager, the West Main Historic District condo indicates 1 day stay policy at this condo. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for West Main Historic District condo?
Based on the information reported by the owner or manager, details for the cancellation policy for the West Main Historic District condo are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
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