Deaconess Guesthouse - Historic Riverfront Luxury Near Derby and Bourbon Trail
Welcome to Deaconess Guesthouse, a rare 1800s historic landmark thoughtfully restored into a luxury riverfront estate by Charming Vacation Homes. Located along the Ohio River, this one-of-a-kind home blends historic charm with modern comfort, offering river views and a highly walkable location ideal for unforgettable group stays.
Enjoy walking access to downtown Jeffersonville restaurants, cafes, shops and seasonal festivals, or stroll across the iconic Big Four Bridge into downtown Louisville for Waterfront Park, bourbon distilleries, Museum Row, live music and nightlife. The home is just minutes from Churchill Downs, making it a prime location for Kentucky Derby events and Bourbon Trail experiences.
This expansive eight bedroom, six bathroom estate comfortably sleeps up to twenty four guests and is designed for elevated group travel. Guests enjoy spa-inspired bathrooms, thoughtfully designed bedrooms and multiple indoor and outdoor gathering spaces that balance privacy with connection.
Luxury amenities include a private hot tub, riverside fire pit, wraparound porches and balconies, a stargazing dome and ample on-site parking.
Perfect for Derby weekends, bourbon tours, corporate retreats, wedding gatherings and family reunions, Deaconess Guesthouse offers a rare blend of history, luxury and location. Book your stay 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)
- Churchill Downs (DERBY) - 7.7 miles (15 mins)
- Downtown Louisville/ 4th Street Live - 2.4 miles (6 mins)
- KFC Yum Center - 2.3 miles (7 mins)
- Waterfront Park - 3.4 miles (9 mins)
- Louisville Airport - 8.6 miles (10 mins)
- Papa Johns Stadium (Cardinal Stadium) - 6.4 miles (11 mins)
- Kentucky Fairgrounds - 6.5 miles (10 min)
- University of Louisville - 6.5 miles (12 mins)
- Kentucky Exposition Center - 6.7 miles (11 mins)
- Kentucky Kingdom - 7.4 miles (13 mins)
- Highland Festival Grounds - 8.5 miles (12 mins)
- Louisville Mega Cavern - 10.2 miles (19 mins)
- Ford LAP Plant - 10.9 miles (16 mins)
- UPS Worldport - 11.2 miles (20 mins)
- Waverly Hills Sanatorium - 17 miles (30 mins)
- Valhalla Golf Club - 19 miles (27 mins)
PROPERTY HIGHLIGHTS
★ Riverfront Luxury Retreat: Wake up to peaceful Ohio River sunrises and unwind with serene waterfront evenings in this rare riverfront home near Louisville and the Bourbon Trail.
★ Prime Walkable Location: Steps from Jeffersonville cafes, parks, shops and dining, with an easy walk across the Big Four Bridge into downtown Louisville. Just 15 minutes to Churchill Downs for the Kentucky Derby.
★ Historic Charm with Modern Elegance: A beautifully restored landmark blending timeless architecture with upscale finishes, designer furnishings and modern comforts.
★ Ideal for Groups and Derby Stays: Eight spacious bedrooms, six spa-inspired bathrooms and multiple gathering areas offer privacy and comfort for families, friends and Derby groups.
★ Four Full Kitchens: Perfect for large groups, multi-family stays or extended visits, with premium appliances and ample space for entertaining.
★ Indoor and Outdoor Living: Enjoy covered porches, private balconies and riverfront seating for relaxing mornings and evenings.
★ Private Backyard Oasis: Features a hot tub, waterfront fire pit, gazebo dining area and lawn games for unforgettable group moments.
★ Entertainment for All Ages: Smart TVs, fast WiFi, cozy lounges and indoor and outdoor games.
★ Kid and Pet Friendly: Thoughtfully designed to welcome families and furry companions.
★ Unmatched Bourbon Trail and Derby Location: A one-of-a-kind luxury stay offering space, comfort and a prime location for Bourbon Trail adventures and Kentucky Derby experiences.
★ 2026 TOP EVENTS
- 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 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
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!
