Title: The Winston on Market - Private Luxury Rental Space - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # The Winston on Market - Private Luxury Rental Space Condo with kitchen, 6-minute walk to Louisville Slugger Museum ## Photo gallery for The Winston on Market - Private Luxury Rental Space ![Interior - The Winston on Market - Private Luxury Rental Space (Louisville)](https://images.trvl-media.com/lodging/115000000/114410000/114401700/114401642/5027a5b8.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - The Winston on Market - Private Luxury Rental Space (Louisville)](https://images.trvl-media.com/lodging/115000000/114410000/114401700/114401642/acf49c9a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - The Winston on Market - Private Luxury Rental Space (Louisville)](https://images.trvl-media.com/lodging/115000000/114410000/114401700/114401642/d85b8696.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Lobby - The Winston on Market - Private Luxury Rental Space (Louisville)](https://images.trvl-media.com/lodging/115000000/114410000/114401700/114401642/908c6246.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - The Winston on Market - Private Luxury Rental Space (Louisville)](https://images.trvl-media.com/lodging/115000000/114410000/114401700/114401642/2457fd4f.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Close to Kentucky International Convention Center and Louisville Slugger Museum, The Winston on Market - Private Luxury Rental Space provides amenities like laundry facilities. Treat yourself to a massage or other spa services. Guests can connect to in-room WiFi. ### Entire condo 2 bedrooms1 bathroom2000 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Air conditioning - Parking available - Fireplace ## Add dates for prices Check-in Check-out Travellers ## 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 condo: WiFi ### Parking and transportation - Wheelchair-accessible parking available ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Microwave - Oven - Refrigerator - Stovetop ### 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 - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - 1 accessible parking space - Elevator - Wheelchair-accessible parking - Wheelchair-accessible path of travel - Wheelchair-accessible path to elevator - Smoking not allowed ### 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) - Fire extinguisher ### General - At least 80% lighting from LEDs - Energy-saving switches in guestrooms - Recycling - Unit size: 2,000 square feet - Water-efficient toilets ## Similar properties ![Smart TV, books](https://images.trvl-media.com/lodging/98000000/97080000/97077700/97077609/ab8d7e4a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee! 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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 there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher 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 neighborhood in Louisville, is home to this condo. The area's natural beauty can be seen at Louisville Mega Cavern, while Louisville Slugger Museum and KFC Yum Center are cultural highlights. Check out an event or a game at Churchill Downs, and consider making time for Kentucky Kingdom, a top attraction not to be missed. [Visit our Louisville travel guide](https://www.expedia.ca/Louisville.dx603002) [View more Condo rentals in Louisville](https://www.expedia.ca/Louisville-Condos.d603002-aaCondos.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=38.257286,-85.75632&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:c_phF%7EgljO%3FS%3FS%3FS%40S%40S%3FS%40S%40S%40SBS%40QBSBS%40SBQBSDQBSBQDSDSBQFQDQDQDQFQFQDQFOFQFQHOFQFMHQFOHOHMHOHOHMJOHMJMHMJMJMJKJMHKLKJKJKLMJILIJKLILILIJILILGLGNGLILELGNELENGLELCNENELCNCNELANCNANCN%3FLANCN%3FNAL%3FN%3FN%3FN%3FN%40N%3FNBL%40N%3FNBN%40NBL%40NDNBLBNDLDNBLDNFLDLFNDLDLHLFNFLFJJLFLHLHJHLJLHJHLLJJJJJJJJJLJJJLJLHLJLHLJNHLHNHNHLFNHNHPFLFPHNFPFPFNDPFPDPFPDPDPDPDPDRBRDPBRDPBR%40PBRBRBR%40P%40RBR%40R%40R%3FR%40R%3FR%40R%3FR%3FR%3FR%3FRAP%3FRAR%3FRARARCRARARCRCRCRAPCREPCREPCREPEPEPEPERGPEPGNEPGPGNGPIPGNGNINIPGLINILININKLILKNILKLKJKJKLKJKLKJKJMJKHMJMHKHMJMFMHKHMFOFMFMHMFODMFMDODMDODMDOBMBODOBM%40OBOBO%40O%40M%40O%40O%3FO%40O%3FO%3FO%3FM%3FOAO%3FOAMAOAOAOCOCMAOCOEMCOCOEMEMEOEMEOGMEMGMIOGMGMGMIKIMGMKMIKIMKKIMKKKKKMMIKKMKKKKKMIMKOIMKMIOIOIMIOIMGQIOGOGOIQGQGOGQEQGOGQEQESEQGQCQEQESCQCSEQCSCQASCSCSASCSASASAS%3FSASAS%3FQ%3FS%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=rQTqPE-CKFDvl4uuxq70K7oiA_E=) Louisville, KY ### What's nearby - ![Muhammad Ali Center showing night scenes and modern architecture](https://images.trvl-media.com/place/6062649/37bc13aa-c0fa-4731-9dbc-637f0a6b0590.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Muhammad Ali Center 3 min walk \- 0.3 km - ![Louisville Slugger Museum showing interior views](https://images.trvl-media.com/place/6062643/2e2ca54c-8bc7-408e-ab83-9666201d4950.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Louisville Slugger Museum 5 min walk \- 0.4 km - ![Panorama Ohio River waterway riverboats and bridges leading to heart of downtown Louisville KY](https://images.trvl-media.com/place/6140365/7abc2e76-97fc-4220-85b3-22fc7e888802.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) KFC Yum Center 8 min walk \- 0.7 km - 21c Museum Hotel 2 min walk \- 0.2 km - Kentucky International Convention Center 6 min walk \- 0.6 km ### Getting around - Louisville, KY (LOU-Bowman Field) 15 min drive ### Restaurants - Heine Brothers' Coffee 2 min walk - Steak And Bourbon 4 min walk - Vincenzo's Italian Restaurant 2 min walk - Mussel & Burger Bar 3 min walk - Sunergos Coffee and Espresso Bar 3 min walk ## Frequently asked questions ### Is The Winston on Market - Private Luxury Rental Space pet-friendly? ### How much does it cost to stay at The Winston on Market - Private Luxury Rental Space? ### How much is parking? ### What time is check-in at The Winston on Market - Private Luxury Rental Space? ### What time is check-out at The Winston on Market - Private Luxury Rental Space? ### Where is The Winston on Market - Private Luxury Rental Space located? ## Have a question? 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