DERBY 2026 DEALS — NOW OPEN!
Book Deaconess Guesthouse, a luxury 8BR/6BA riverfront estate. Enjoy 4 private suites with full kitchens, elegant lounges, balconies and beautifully restored historic charm - perfect for groups and multi-family stays. Walk to downtown Jeffersonville, cross the bridge to Louisville and reach Churchill Downs in minutes. With premium amenities and unbeatable access to bourbon, dining and waterfront fun, your exclusive Derby escape starts here - reserve now!
The space
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Deaconess Guesthouse - A Landmark Riverfront Escape ~Walk to Downtown Jeffersonville / Louisville
~ Derby 2026 discounted dates still available ~
Step into one of Jeffersonville’s most iconic stays—an 1800s historic landmark reimagined into a luxury riverfront estate by Charming Vacation Homes. With sweeping Ohio River views, timeless architecture, and a rare walkable location, Deaconess Guesthouse delivers an exclusive blend of history, comfort and high-end hospitality for unforgettable group getaways.
★ Unbeatable Location, Built for Adventure
Stroll to downtown Jeffersonville’s best dining, cafés, shops, and festivals—or walk the Big Four Bridge into Louisville for Museum Row, Waterfront Park, bourbon tastings, live entertainment and more. You’re minutes from Churchill Downs, the Bourbon Trail, and the region’s top attractions, then back home to your private riverfront sanctuary.
★ Designed for Groups Who Want It All
This expansive 8-bedroom, 6-bath estate sleeps up to 24 with beautifully curated bedrooms, spa-inspired baths and multiple lounge spaces—perfect for privacy, connection and celebration.
★ Signature Amenities
• Private hot tub
• Riverside fire pit
• Wraparound porches + riverfront balconies for sunrise coffee and sunset bourbon
• Stargazing Dome (guest favorite)
• Ample on-site parking
Whether it’s a corporate retreat, wedding weekend, milestone celebration, or family reunion, Deaconess Guesthouse is more than a stay—it’s a one-of-a-kind experience where luxury meets location, and every moment feels elevated. Reserve your dates today.
** Please note: A strict cancellation policy applies for Derby and Bourbon & Beyond dates. **
★ CONVENIENT LOCATION
The house is centrally located and is within a 10-15 minute Uber/Lyft drive to most locations:
- Big Four Walking Bridge (Connecting KY and IN) - 0.4 miles (2 mins)
- Downtown Louisville/ 4th Street Live - 2.4 miles (6 mins)
- Waterfront Park - 3.4 miles (9 mins)
- Churchill Downs (DERBY) - 7.7 miles (15 mins)
- KFC Yum Center - 2.3 miles (7 mins)
- Papa Johns Stadium (Cardinal Stadium) - 6.4 miles (11 mins)
- University of Louisville - 6.5 miles (12 mins)
- Churchill Downs (DERBY) - 7.7 miles (15 mins)
- Kentucky Exposition Center - 6.7 miles (11 mins)
- Kentucky Kingdom - 7.4 miles (13 mins)
- Louisville Airport - 8.6 miles (10 mins)
- Highland Festival Grounds - 8.5 miles (12 mins)
- Louisville Mega Cavern - 10.2 miles (19 mins)
- UPS Worldport - 11.2 miles (20 mins)
- University of Louisville - 6.5 miles (12 mins)
- Valhalla Golf Club - 19 miles (27 mins)
- Waverly Hills Sanatorium - 17 miles (30 mins)
PROPERTY HIGHLIGHTS
★ Riverfront Luxury Escape – Wake up to golden Ohio River sunrises and unwind with sparkling waterfront evenings—rare, serene and unforgettable.
★ Prime Walkable Location – Steps to Jeffersonville’s cafés, shops, parks and dining, plus a scenic stroll over the Big Four Bridge into downtown Louisville. Minutes to Churchill Downs and top attractions.
★ Historic Landmark, Modern Luxe – A beautifully restored property that blends timeless character with elevated, designer comfort.
★ Perfect for Groups – 8 stylish bedrooms, 6 spa-inspired baths, and multiple gathering spaces for connection and privacy.
★ Four Full Kitchens – Fully equipped culinary setups with premium appliances—ideal for hosting, multi-family stays and effortless meals.
★ Indoor-Outdoor Living – Sip coffee on covered porches, relax on private balconies, and enjoy the calming rhythm of riverfront days.
★ Private Backyard Oasis – Soak in the hot tub, gather by the waterfront fire pit, dine in the gazebo/Hyperdome and enjoy lawn games together.
★ Entertainment for Every Age – Cozy lounges, Smart TVs, fast Wi-Fi, and indoor/outdoor games keep everyone entertained.
★ Kid & Pet Friendly – Thoughtful amenities for little ones and furry companions so the whole crew feels at home.
★ A One-of-a-Kind Waterfront Stay – Exclusive, spacious, and perfectly located—crafted for memorable getaways and repeat visits.
★ 2026 TOP EVENTS
- Dinosaur World Live – Jan 23, 2026
- The Millennium Tour – Jan 23, 2026
- Bluegrass World of Wheels – Jan 24–25, 2026
- NouLou Chamber Players – Feb 2, 2026
- The Great Gatsby – Feb 10–15, 2026
- Cody Johnson – Feb 14, 2026
- Kindle the Flame – Feb 14, 2026
- USA Gymnastics Winter Cup – Feb 20–22, 2026
- Bourbon Classic – Feb 25–28, 2026
- LDB Fest – Feb 27–28, 2026
- America: Happy Trails Tour – Apr 2, 2026
- Thunder Over Louisville – Apr 18, 2026
- Great Steamboat Race – Apr 29, 2026
- Kentucky Oaks – May 1, 2026
- Kentucky Derby – May 2, 2026
- World Oddities Expo – Jun 13–14, 2026
- Run 4 Roses - Jul 9-14, 2026
- Kentucky State Fair – Aug 20–30, 2026
- Big Four Art Festival – Sep 12–13, 2026
- Louder Than Life – Sep 17–20, 2026
- Bourbon & Beyond – Sep 24–27, 2026
- St. James Court Art Show – Oct 3–4, 2026
- NuLu Fest – Oct 9–11, 2026
- Halloween & Haunted Attractions – Oct 24–31, 2026
- Thanksgiving Week Travel – Nov 25–29, 2026
- Light Up Louisville – Nov 27, 2026
- Christmas at Frazier Museum – Dec 5–20, 2026
- Louisville Ballet: The Nutcracker – Dec 2026
- New Year’s Eve at Fourth Street Live! – Dec 31, 2026
★ 2026 TRADE SHOWS & EXPOS
- Louisville Manufactured Housing Show — Jan 14–16, 2026
- NVP Product Expo — Jan 22–25, 2026
- Louisville Boat, RV & Sportshow — Jan 28–Feb 1, 2026
- Show of Shows (Military Antiques) — Jan 29–Feb 1, 2026
- National Farm Machinery Show — Feb 11–14, 2026
- Ace Hardware Spring Convention — Feb 24–26, 2026
- GAMA Expo — Mar 1–5, 2026
- Mid-America Trucking Show (MATS) — Mar 26–28, 2026
- Connect Spring Marketplace — Apr 14–16, 2026
- World Oddities Expo — Jun 13–14, 2026
- Equip Expo — Oct 20–23, 2026
★ OPTIONAL CONCIERGE ENHANCEMENTS
Make your stay even more effortless:
1. Grocery Pre-Stocking – Walk into a fully prepared kitchen.
2. Private Chef Experience – Perfect for celebrations or elevated evenings in.
3. Custom Bourbon Tours & Chauffeur Services – Personalized for your group.
★ PEACE OF MIND AND EXCEPTIONAL GUEST COMFORT
- Professionally cleaned and sanitized
- Contactless self check-in for your convenience
- 24/7 guest support throughout your stay
- Exterior-only security cameras at the front of the home for guest safety and property protection
Guest access
Guests self check-in with keypad. You will receive an access code 24-48 hours prior to checkin.
Other things to note
NOTE:
1. 25+ to book.
2. House Rules Required: E-sign rental agreement and submit a $500 security hold via secure OwnerRez (placed 2 days before arrival, released 7 days after departure if no damage).
3. Strict cancellation for Derby & Bourbon & Beyond dates.
4. No visitors unless pre-approved by the host.
5. Exterior cameras only (parking area & front door). No interior or backyard cameras.
6. Dome use: Not recommended during hot summer months.
7. No early check-in / late check-out on same-day turnovers.
8. When available: $100 (≤2 hrs), $250 (2–4 hrs), full night rate (>4 hrs).
9. Non-Airbnb refunds incur a 3% Stripe processing fee.
PLEASE REVIEW THE HOUSE RULES BEFORE BOOKING. THANKS!!
