Pet-friendly holiday rentals in Shepherdsville

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland and High Park cattle, a horse, friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

Lilly's Pad

Relax and unwind in between all your Louisville activities. We are close (4.4miles) from SDF airport ,and I65 and the Gene Snyder Freeway are less than 8miles away. There are a plethora of activities from shopping to entertainment venues such as horse racing at historic Churchill Downs, Louisville Zoo, Kentucky Kingdom amusement park, Muhammad Ali museum and childhood home, Louisville Slugger Museum, Valhalla golf club, and 36 Bourbon Distilleries as well as cave exploring and fishing.

Sunshine and Whiskey

We are located in the heart of the bourbon capital of the world. If your looking for a peaceful quiet country night we are the place for you. We offer a queen size bed and small pull out sofa. There are several local attractions we are 6 miles from Makers Mark, 11 miles to Log Still, 3 miles from the XB Arena (Saturday nights Nov-March), and 13 miles to Historic Bardstown to include Heaven Hill. At night you can relax under our grain bin gazebo. Horse stalls available for $25

Pickleball*Hot tub*Speakeasy*Bourbon*Pet-Friendly

The Bourbon Skyline is your passport to an unforgettable Kentucky experience. This newly renovated 4-bed, 3 full bath ranch sitting on 8 acres is the epitome of comfort and Kentucky charm. The Bourbon Skyline's hilltop location offers beautiful views over Kentucky landscapes. It's the best of both worlds; countryside, & close to everything! Outdoor dining, fire table & hot tub, corn hole and Pickleball! Just a short drive to Louisville, Lexington, Mammoth Cave & so much more!

✸ Bright, Modern 3BR | Etown Sports Park 1.8 mi✸

Have fun with the whole family at this modern, stylish place! Minutes to downtown Elizabethtown, less than 2 miles to Elizabethtown Sports Park and Bluegrass Sportsplex, convenient to I-65, and an easy drive to Fort Knox make it a desirable location. Luxury latex foam mattresses and smart TVs in the suite rooms, brand new paint and hardwood look flooring throughout, immaculate cleaning, and smart air purifiers will make you never want to leave! 2 car attached garage.

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.

Parkside Pad - Iroquois Park

Central Location! One bedroom & One Bath Home. This home offers a 5 minute walk to wonderful Iroquois Park and the charming Beechmont Neighborhood. Short 5 minute drives to Churchill Downs and the University of Louisville, 10 minute drives to the Airport and Fairgrounds/Exposition Center, and 15 minute drives to trendy NuLu, Highlands, and Germantown neighborhoods. This space will offer the best of what Louisville has to offer.

WynDown Spot

Wind down at this centrally located patio home that comes with an attached garage. This wine-themed home is open and airy, and has a screened-in patio for guests to enjoy. Located 0.2 miles from I-65 and minutes away from grocery stores and restaurants. Forest Edge Winery, James Beam Distillery, and MillaNova Winery are a 10-15 minute drive and many other attractions are nearby. You and your pets can "wine down" at Wyandot!

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

Pastel Tiny Home • Romantic Retreat on 15 Acres

💖 Escape the city buzz without leaving Louisville. Wake up to 15 acres of rolling hills, explore mowed walking paths, and unwind on your private deck by the fire pit. Perfect for nature lovers and 'Louisville Loop' cyclists looking for a cozy, intentional stay. Experience the charm of country living—you’ll hear the occasional train and see our resident groundskeeper (my dad, Martin!) tending to the land.🌙🌿

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.

Kentucky Derby Guest House

The Kentucky Derby guest house is an affordable place to stay that’s comfortable with plenty of room. Sleeps 6 comfortably with 3 queen beds w/ linens but there is plenty of room for more guests with SELF SUPPLIED air mattresses and bedding, we do not supply them. Great for an overnight stay on a road trip , or a multi day getaway while you’re in Kentucky visiting the Bourbon Trail.