When it comes to planning a trip, picking the perfect destination can be tricky, especially if you’ve been lucky enough to have spent enough time on the beach that you’re ready to find something new. So let me ask you this… do you like Bourbon? If so, a trip to Kentucky to check out the Bourbon Trail may be in the cards.
The Bourbon Trail gives travelers a chance to hit multiple cities in the Commonwealth of Kentucky while exploring the birthplace of bourbon, with lots of reasonably priced places to stop along the way. If you’re looking for help setting your path, looking for different distilleries to check out, or just seeking out more information about the Bourbon Trail before you hit the road, we’ve got you covered! Once you’re ready to roll, check out one of — or all of — the dozen options we’ve selected to push you along the Bourbon Trail while on your trip through the Bluegrass State. These rental suggestions are mostly for couples, but you’ll notice a few larger options towards the end of the trail — just in case you’ve made some friends along the way!
Vacation Rentals In Louisville, Kentucky
The Main Suite, Louisville$165/nightly avg
The Main Suite is a newly renovated studio on the second floor of The 713 in Louisville. Experience the historic building overlooking Main Street through the amazing floor-to-ceiling windows. This cozy unit has a single sleeping area and is ADA-accessible. A perfect place to start your Bourbon Trail tour, The Main Suite is in close proximity to bourbon tours, museums, the Center for the Arts, and more. Updated and ready for you, be sure to check out the photos!
River City Loft, Louisville$135/nightly avg
Since you will no doubt find the need to spend a second night in Louisville, the River City Loft might be the ideal 925-square-foot spot for you. This one-bedroom loft is in the heart of downtown Louisville and is within walking distance to shops, restaurants, bars, and more. Enjoy free parking in the secured parking garage.
Cassius Quarters, Louisville$819/nightly avg
Look, there are a lot of places to check out in Louisville, okay? Now, it’s day three — you’re still in Louisville, still on the Bourbon Trail, and your tour group is getting bigger. No problem! With four bedrooms and space for 10 or more, Cassius Quarters is exactly what you’d expect on Historic West Main. This space is gorgeous, spacious, and you’re going to love the river views from the private balcony. This apartment does have six steps going from the front of the building to the back, so take note if you have any mobility issues.
Vacation Rentals In Shepherdsville, Kentucky
The Clubhouse, Shepherdsville$144/nightly avg
When your Bourbon Trail journey takes you to Shepherdsville, The Clubhouse is the perfect spot to relax. With an open-floor plan and 10-foot ceilings, this home has all the amenities you need and is conveniently located near restaurants and attractions. There are Bourbon Trail stops and wineries nearby. Questions? Your hosts are Louisville natives — ask away!
Vacation Rentals In Owensboro, Kentucky
The Haven on Hill Avenue, Owensboro$160/nightly avg
Welcome to Owensboro! Whether you’re looking for a spot for a couple or a larger group, The Haven on Hill Avenue has four bedrooms and can sleep up to eight people. Located on the Dogwood/Azalea Trail, this home is in a quiet neighborhood near parks, shopping, and more. Be sure to visit the Green River Distilling Co. when in town!
Vacation Rentals In Bardstown, Kentucky
Bourbon Trail Cottage, Bardstown$125/nightly avg
The Bourbon Trail Cottage is a unique cottage nestled in the woods along the Bourbon Trail just outside of Bardstown. Enjoy the queen-sized bed, propane fireplace, outdoor fire pit, high-speed internet, and lots of other amenities. It’s all just minutes from the Jim Beam Distillery, Four Roses Bourbon Warehouse and Bottling Tour, and more! Bardstown is a bit more rural than some other spots, so be sure to read up on the area so you’re best prepared for your visit.
Huston House, Bardstown$250/nightly avg
Sticking around Bardstown one more night? Check out Huston House! Just steps from historic Main Street, this two-story townhome is in the heart of downtown Bardstown. You’ll love the private courtyard, full-sized garage, and lots of other amenities that offer you tons of relaxation after a day of distillery tours. Book this one soon!
Vacation Rentals In Lebanon, Kentucky
Downtown Abode, Lebanon$150/nightly avg
Next stop — Lebanon! Well, maybe not your next stop (go in whatever order you choose!), but a stop nonetheless. The Downtown Abode is located in the heart of downtown Lebanon, less than an hour from eight Bourbon Trail distilleries. When staying at this three-bedroom, handicap-accessible (no steps to enter the house) home, you’re within walking distance of several restaurants. This spacious house is sure to impress!
Vacation Rentals In Danville, Kentucky
Wilderness Trail Bungalow, Danville$156/nightly avg
Featuring cedar shake siding, hardwood floors, and charming decor, this two-bedroom bungalow was completely remodeled in 2022. It is just a couple of blocks off of Main Street, which is home to quaint storefronts, local eateries, pubs with craft beer, and Copper & Oak, which serves 50 bourbons! Danville’s very own distillery, Wilderness Trail, is nearby as well.
Vacation Rentals In Lawrenceburg, Kentucky
The Green Cabin, Lawrenceburg$180/nightly avg
Not far from Danville is Lawrenceburg, where you can enjoy a relaxing stay at the Green Cabin — located in the heart of bourbon and horse country. This charming spot, situated on 9 acres, is near the Wild Turkey and Four Roses distilleries on the Bourbon Trail. Buffalo Trace, although not a part of the Bourbon Trail, is also a short drive away. After enjoying the area, come back to the cabin and enjoy the Jacuzzi tub, gas fireplace, or relax on the three-quarter wrap-around deck. This one is a beauty — be sure to check it out!
Vacation Rentals In Lexington, Kentucky
Gratz Park Place, Lexington$1,181/nightly avg
On the off chance that you’ve made it all the way to Lexington on your Bourbon Trail adventure and made lots of friends along the way, Gratz Park Place is the perfect spot for you and your group of up to 12. In a neighborhood full of the oldest and most beautiful homes in Lexington, this gorgeous rental is sure to impress. Just a short drive to plenty of attractions, this home is gorgeous and inviting — definitely worth a look!
Top Shelf Condo, Lexington$400/nightly avg
You can’t get any closer to the action than in this condo located on top of Lexington’s Pepper Bourbon Distillery! It is literally on the Bourbon Trail, with another stop, Barrel House Distillery, nearby as well. Offering amenities aplenty, three balconies, and top-shelf views, there isn’t a better place to stay after a long day of bourbon tasting.
Once you’ve had your fill of bourbon, check out more things to do while in Kentucky: