Vacation rentals in Pioneer Village

second floor 1 bedroom + office W/D & easy parking

This duplex is nestled in the quiet and peaceful community of Zoneton. Offering the benefit of a suburb setting and only being 17 minutes away from Louisville's greatest attractions including downtown, Churchill Downs and Jim Beam Bourbon Trail. The great room boasts a full accessorized kitchen, wet bar, pull out queen sofa with memory foam & a 65" Smart TV. The bedroom has a king adjustable bed, smart TV and walk-in closet. Unit also has a dedicated office! There is Fiber optic WIFI & Netflix.

The Barrel Proof Bungalow

This stylish 3 bedroom 2 bathroom home on the "Kentucky Bourbon Trail" has been a labor of love and full remodel down to the studs. The Barrel Strength Bungalow is centrally located between Interstate 65 (Jim Beam) and Bardstown's city center. A unique outdoor living space with one of a few hot tubs in Bardstown area Airbnb's. Also offers a firepit, outdoor grill and patio area. More than 15 distilleries within an hour's drive and approximately 30-35m to Downtown Louisville and Churchill Downs.

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

Cozy Studio in Brooks

Step in to a bright and cozy studio apartment with Moroccan flair and seasonal decor. We're only 20 minutes from downtown Louisville and world-famous Churchill Downs, 15 min. from the SDF airport, KY Expo Center and Bernheim Forest and 10 min. from miles of Jefferson Memorial forest trails. Located on a peaceful country hillside with a separate entrance and a high outside deck that opens to the treetops, it's the perfect place to relax but still be close to all that Louisville has to offer.

Cozy Home Near the Bourbon Trail & KY Derby

Welcome to our spacious 4-bedroom home, located between Kentucky’s iconic Bourbon Trail and all that Louisville has to offer. Just a few minutes drive to I65 close to E-town, Bardstown or Louisville. Nestled in a small, quiet neighborhood, comfortable and convenient for families, friends, or groups looking to explore the heart of Kentucky. Whether you’re here for bourbon, events, the Kentucky Derby, or relaxation, this home is your perfect getaway. Book now to make unforgettable memories!

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

The Dark Horse: Western Gothic Gem near Expo/SDF

🖤 Welcome to The Dark Horse—a Western Gothic retreat where moody elegance meets frontier soul. With 3 bold bedrooms, a full kitchen, grand dining room, and luxe living space, it's perfect for unforgettable group stays. Outside, unwind on the covered porch, grill at the outdoor bar, or gather by the fire pit. Fenced yard, dramatic design, and modern comfort—crafted for connection, slow evenings, and stories that linger long after you leave. Your escape begins here. 🤠🖤

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!

Flawlezz Stays

Kick back and relax in this calm, stylish space. Flawlezz Stays provides a home away from home, with gorgeous views of the downtown louisville skyline. This unit is very spacious, safe, very clean and accommodated with everything you will need during your luxurious stay. It's rooftop accessible with a entertainment hub and more. Scenic trails along the Falls of Ohio State Park. Some of the best restaurants just minutes away.