The Winston on Market - Private Luxury Rental Space

Interior
Private kitchen
Private kitchen
Lobby
Private kitchen
Don't miss out! Price and availability may change

Apartment in Jefferson County, KY

6 guests · 2 bedrooms · 1 bath

Reasons to book

High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Includes essentials and more

About this apartment rental

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*

Amenities at The Winston on Market - Private Luxury Rental Space

Non-smoking
No pets allowed
Family friendly

Map of Jefferson County, KY


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FAQs

Is parking included with this apartment?

Parking is not specified as an available amenity at The Winston on Market - Private Luxury Rental Space. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

We didn’t find pool listed as an amenity for this apartment. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this apartment is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Winston on Market - Private Luxury Rental Space?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.