Deaconess Guesthouse - Historic Waterfront Luxury Near Jeffersonville and Louisville Downtown
Deaconess Guesthouse is a rare historic riverfront luxury estate perfectly located near the Kentucky Derby and the Bourbon Trail. This beautifully restored 1800s landmark by Charming Vacation Homes blends timeless character with modern comfort along the Ohio River in the heart of Jeffersonville.
Enjoy walkable access to local restaurants, cafes, shops and festivals, or stroll across the Big Four Bridge into downtown Louisville for Waterfront Park, bourbon distilleries, museums, live music and nightlife. Churchill Downs is just minutes away, making this an ideal home base for Derby events and bourbon experiences.
The expansive eight bedroom six bathroom home sleeps up to twenty four guests and is designed for elevated group stays with spa style baths, elegant bedrooms and multiple indoor and outdoor gathering spaces.
Luxury amenities include a private hot tub, riverfront fire pit, wraparound porches and balconies, a stargazing dome and ample parking. Ideal for Derby weekends, Bourbon Trail trips, corporate retreats and family gatherings. Book your unforgettable 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)
- Downtown Louisville/ 4th Street Live - 2.4 miles (6 mins)
- Churchill Downs (DERBY) - 7.7 miles (15 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)
- University of Louisville - 6.5 miles (12 mins)
- Kentucky Fairgrounds - 6.5 miles (10 min)
- 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)
- Valhalla Golf Club - 19 miles (27 mins)
- Waverly Hills Sanatorium - 17 miles (30 mins)
PROPERTY HIGHLIGHTS
★ Luxury Riverfront Home Near Louisville and Bourbon Trail: Enjoy stunning Ohio River sunrises and peaceful waterfront evenings in this rare riverfront retreat near downtown Louisville and top Bourbon Trail distilleries.
★ Walkable Jeffersonville Location: Steps to cafes shops parks and dining with an easy walk across the Big Four Bridge into downtown Louisville and only 15 minutes to Churchill Downs for the Kentucky Derby.
★ Historic Home with Modern Comforts: Beautifully restored landmark featuring upscale finishes designer furnishings modern kitchens and premium amenities throughout.
★ Ideal for Large Groups and Derby Stays: Eight bedrooms six spa style bathrooms and multiple living areas perfect for families friends corporate retreats and Derby groups.
★ Four Full Kitchens: Perfect for multi family stays extended visits and entertaining with high end appliances and generous dining space.
★ Indoor and Outdoor Living Spaces: Covered porches private balconies riverfront seating hot tub fire pit gazebo dining and lawn games.
★ Family and Pet Friendly: Thoughtfully designed for kids pets and multigenerational stays.
★ Prime Derby and Bourbon Trail Location: A one of a kind luxury stay offering space comfort and unbeatable access to the Kentucky Derby Bourbon Trail and downtown Louisville attractions.
★ 2026 TOP EVENTS
- 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
- 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!!
