Stay in History. Immerse Yourself in Elegance.
Welcome to The Winston on Market
Stay in History. Immerse Yourself in Elegance.
Welcome to The Winston on Market
Timeless charm with modern comforts
Nestled in the heart of downtown Louisville, KY, The Winston on Market offers a one-of-a-kind stay and event experience inside the historic Old Portland Building at 539 W. Market Street.
Built in 1882, this beautifully restored gem blends timeless charm with modern comforts, making it the perfect destination for travelers, short-term and long-term rentals, special occasions, and corporate gatherings alike.
Why Choose The Winston on Market?
✔️ Historic Charm – Enjoy the elegance and character of a 19th-century landmark.
✔️ Prime Location – Steps from Louisville’s top attractions, dining, and entertainment.
✔️ Versatile Event Space – Ideal for baby showers, meetings, workshops, pop-ups & more.
✔️ Comfort & Convenience – Modern amenities wrapped in vintage beauty.
✔️ Complete Privacy – Private elevator access & secured weekend entry.
✔️ Easy Parking – Street parking, adjacent lot & two nearby garages (pay-to-park).
Why Choose The Winston on Market?
✔️ Historic Charm – Enjoy the elegance and character of a 19th-century landmark.
✔️ Prime Location – Steps from Louisville’s top attractions, dining, and entertainment.
✔️ Versatile Event Space – Ideal for baby showers, meetings, workshops, pop-ups & more.
✔️ Comfort & Convenience – Modern amenities wrapped in vintage beauty.
✔️ Complete Privacy – Private elevator access & secured weekend entry.
✔️ Easy Parking – Street parking, adjacent lot & two nearby garages (pay-to-park).
Book Your Stay
Whether you’re visiting Louisville for business, pleasure, or a bit of both, The Winston provides the perfect home away from home. Our luxurious private suite is thoughtfully designed to offer comfort, convenience, and style, ensuring a restful and enjoyable stay. From modern amenities and cozy furnishings to a quiet, private setting, every detail is tailored to meet your needs. Whether you’re unwinding after a day of meetings or gearing up for a night out in the city, The Winston is your ideal retreat in the heart of Louisville. Book your stay today and experience elevated comfort like never before.
Amenities Include:
- 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′ Ceilings
- Panoramic view of the city
- 10′ windows
- Private Elevator Access
- AV Sound System
Pricing
Click on the button below for rental breakdown.
Customize your stay on-site
- Personal Chef Services
- Mobile Massage Therapy Services
- Make-up Artist
- Other services by request
*Contact us for pricing
Amenities Include:
- 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′ Ceilings
- Panoramic view of the city
- 10′ windows
- Private Elevator Access
- AV Sound System
Pricing
Click on the button below for rental breakdown.
Customize your stay on-site
- Personal Chef Services
- Mobile Massage Therapy Services
- Make-up Artist
- Other services by request
*Contact us for pricing
Book Us On:
Gallery
Rave Reviews
★★★★★
Contact Us
Ready to Book Your Experience at The Winston on Market?
We’d love to host you! For inquiries, availability, or special requests, please fill out the form below or contact us directly.
For the quickest response, give us a call at 502-627-0147.
We’re here to make your stay unforgettable.
Location
The Old Portland Building
539 W. Market St Suite #200
Louisville, KY 40202
Hours of operation
Tours & viewings by appointment only