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Bourbon barrels at a distillery along the Bourbon Trail in Kentucky
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  • DestinationsUnited StatesKentucky

    12 Best Places To Stay Along The Bourbon Trail

    Jeff Stahlhut
    August 20, 2022

    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.

    Videos by TravelAwaits

    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!

    Dreaming of Louisville – your dream vacation awaits you
    24 reviews
    Apartment
    3 Guests
    1 Bathroom
    Top guest reviews
    Overall enjoyed our stay very much! Walking distance to several fun activities, parking was convenient and inexpensive, great restaurants nearby and property was very chic and clean. Only inconveniences are outside the property management’s control such as entry into the building via keypad that was very hard to read at certain times because of sunlight (locked myself out at one point), little space to unpack/store clothing (it is a studio) and we had a family staying above us that were apparently raising track stars as the kids were constantly running. If we ever travel back to Louisville we would definitely choose this property!
    We loved our stay and will be back. The owners had great recommendations for places to eat & shop! With 2 coffee shops nearby, (next door & across the street) we had a relaxing happy morning.
    We stayed here for two nights as the start of the Bourbon trail. Place was everything that was stated. Easy walking distance to all the attractions we interested in. Thanks so much
    Great place with a fantastic location.
    It was a perfect and convenient location to attend a conference at the convention center as well as touring the area. Many downtown amenities were walkable and we enjoyed meeting the Queen (the housekeeper)!
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    from USD 165
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    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.

    Dreaming of Louisville – your dream vacation awaits you
    97 reviews
    Condo
    2 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    The apartment was awesome. Most importantly my wife loved it. Unique character with all things modern
    This is a great 3rd floor apartment. Close to lots of stuff but removed from the noise below. The apartment is perfect if you are looking to stay in downtown Louisville.
    Awesome charm and feel. Small enough to feel cozy but feels bigger due to its open concept. The balcony was a added bonus and the property provided tons of music and movies and books as well as some comforts. I also enjoyed the local recommendations. We tried a breakfast place and was in love. Will definitely be back. No cons for us.
    Exceeded my expectations!! Beautiful place. The music library was a wonderful surprise. The loft is gorgeous and I had everything I needed at my fingertips.
    I cannot express how wonderful this city loft was! The place was perfect and Justin was a fantastic host! Thank you, thank you, thank you!!!!
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    from USD 135
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    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.

    Dreaming of Louisville – your dream vacation awaits you
    27 reviews
    Apartment
    13 Guests
    4 Bedrooms
    3 Bathrooms
    Top guest reviews
    This place is beautiful and the location is perfect.
    Could not have asked for a better stay in Louisville. Steps from the Louisville Slugger and Muhammad Ali museums. Great eateries and bourbon tasting rooms as well. Balcony with river views, all modern finishings. Definitely recommending to friends.
    We had a boys weekend in downtown Louisville. This property was perfect for the group. Highly recommend it!
    A group of four guys in our early 50’s stayed here to explore the bourbon trail. There could not be a more perfect property. Every single thing from initial communication, to check-in, to the spotless, cool, centrally located apartment, made this one of the most amazing rental experiences I have ever had.
    Lovely condo in an excellent downtown location. Very secure. Easy walk to bourbon tasting, science center, slugger museum, restaurants. The primary bedroom was unfortunately somewhat noisy with street traffic. Overall an excellent condo rental.
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    from USD 819
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    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!

    Dreaming of Shepherdsville – your dream vacation awaits you
    37 reviews
    Private vacation home
    6 Guests
    3 Bedrooms
    2 Bathrooms
    Top guest reviews
    The house is a convenient drive to both Bardstown and Louisville, we visited both many times on our stay. The house itself is nicely done and the appliances, TV’s, bathrooms, etc all work well. We would definitely stay here again on when we return to Kentucky.
    It’s all you need in a VRBO. It was very clean very comfortable in a safe neighborhood. And communication with the host was spot on.
    Loved this property. The owners were very helpful and everything was great. Loved the close proximity to everything:
    Sheryl and I enjoyed our stay. The property was updated and very comfortable. Everything we needed was supplied. The location provided the privacy and safety we wanted during our stay in Shepherdsville. It was perfect!
    Really enjoyed our stay. Would stay again!
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    from USD 144
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    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!

    Dreaming of Owensboro – your dream vacation awaits you
    18 reviews
    Private vacation home
    8 Guests
    4 Bedrooms
    2 Bathrooms
    Top guest reviews
    We have never rented a house before. Normally we just do a hotel. However, that will be changing. We had a great time here. It was cozy and home feeling. The other couple staying with us also loved it. We couldn’t have asked for better!
    Very nice people, great area
    We had plenty of room. The beds we comfortable. Our granddaughter loved the basket of toys you had at the home. Thanks!
    We love this house. It’s down the street from my mom’s house. Very convenient.
    The house had all the room and amenities for our needs. Very comfortable beds, quiet neighborhood and convenient location. We were pleasantly surprised with the 3 nice bedrooms and 2 full baths on lower level and much more sleeping arrangements upstairs. Highly recommend!
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    from USD 160
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    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.

    Dreaming of Coxs Creek – your dream vacation awaits you
    67 reviews
    Cottage
    3 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    I was such a unique,amazing home. Loved the story about the home. Peaceful area
    Everything you need is in the cabin. It has a beautiful porch to sit out on. The fireplace inside was comforting. I truly wished we could’ve met the owners just to say thank you.
    We really enjoyed the location of this house – and it is beautiful on a beautiful piece of property. We had a little trouble lighting the fireplace and eventually figured it out, but didn’t find the communication with the owner particularly helpful. (It got sorted and it is a lovely fireplace.) Bed and sofa were comfy, kitchen was pleasantly equipped. Shower was great! Outdoor seating was lovely.
    Quiet, unique and clean. We had a relaxing stay! Great fireplace and firepit! Thank you!
    We very much enjoyed our stay! It was clean and the owners were very helpful and kind.
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    from USD 125
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    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!

    Dreaming of Bardstown – your dream vacation awaits you
    157 reviews
    Private vacation home
    4 Guests
    2 Bedrooms
    2 Bathrooms
    Top guest reviews
    Perfect location in the heart of Bardstown! Property was very charming and clean and comfortably accommodated 4 adults. Kim was an excellent host. She was very responsive and knowledgeable about the area. Highly recommended!
    Great property and location. This was our third stay at Kim’s home. Booked for 2023 already. This should tell you something
    Perfect place with everything you could possibly need. Even umbrellas. Great beds. The best!!!
    The location is perfect. We walked downtown. The dinner train and bakery were are favs. We had ample room for 4 people in the home. It was cozy and well-stocked.
    Lovely property, easy access to all areas of Kentucky we wished to visit. One in our party left behind an article. The owner quickly responded and agreed to mail the property to the owner. Fabulous stay!
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    from USD 250
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    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!

    Dreaming of Lebanon – your dream vacation awaits you
    16 reviews
    Private vacation home
    8 Guests
    4 Bedrooms
    2 Bathrooms
    Top guest reviews
    Within walking distance of quant downtown and several places to eat.
    Words can’t describe how great it was staying here while visiting family. They took such care in making us feel welcomed. Even after the stay my daughter left her game boy and they shipped it right to us with no charge to us!!We will definitely stay again and highly recommend!!Also area around us was quite, peaceful coffee on the porch in the morning. And walking distance to the downtown area which shops and restaurants.
    We had a lovely long weekend with out of state family from Ohio and Arkansas. The location was convenient to many excursions and each drive was in beautiful country. The home is well equipped, very comfortable beds and baths. The back yard was very private, shady and welcoming, although we didn’t sit around very much on this trip. The kitchen had what we needed and the living room we lounged in was perfect at the end of the days. The owners could not have been more gracious in welcoming us. Thank you for your lovely home. We hope to visit again.
    This was the perfect place for me and my husband to stay! The house was very clean; it was stocked very well, and so comfortable. The best part was the fenced in back yard for our dog to play in. We enjoyed several nights sitting on the patio and enjoying the outdoors. Thank you Jerry!
    Jerry & Sharon were great hosts who met us upon arrival. Jerry walked us through the house and allowed us to use anything in the house. Jerry provided some great tips on places to eat and good bourbon trail spots to hit.
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    from USD 150
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    Vacation Rentals In Danville, Kentucky

    Wilderness Trail Bungalow, Danville$199/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.

    Dreaming of Danville – your dream vacation awaits you
    5 reviews
    Private vacation home
    6 Guests
    2 Bedrooms
    1 Bathroom
    from USD 199
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    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!

    Dreaming of Lawrenceburg – your dream vacation awaits you
    135 reviews
    Cabin
    6 Guests
    2 Bedrooms
    2 Bathrooms
    Top guest reviews
    The property was well maintained and clean and welcoming inside the house. There were snacks and bottled water available as well as cabinets with everything needed for cooking meals if needed. We didn’t use them. We used coffee makers though. We liked the property.
    Will definitely come back, every thing was beyond perfect!
    Beautiful cabin only a couple miles or less from the small town of Lawrenceburg. Tasteful rustic decor with all the comforts of home. Location was well situated for visiting distilleries on the Bourbon Trail. Owner very helpful and responsive. Highly recommend.
    Awesome place would definitely stay again. Very nice and well kept
    If you are wanting to spend time on the Bourbon Trail or at Keeneland, this is the place to stay if it is available. Everything you need, owners are very kind and the place is very well kept. The location is excellent with internet service but still a rural feel. So much better than a hotel!
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    from USD 180
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    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!

    Dreaming of Lexington – your dream vacation awaits you
    15 reviews
    Private vacation home
    12 Guests
    6 Bedrooms
    5 Bathrooms
    Top guest reviews
    Great place, excellent location.
    Unit is nicely updated and absolutely spotless. Very generous of owner to leave K-cups, cleaning supplies, and waters in the refrigerator. Only thing I would suggest is that the 4th floor skylights have blinds installed to keep out the hot afternoon sunshine.
    This was the perfect spot for a guys trip to bourbon country. Great location and walkable to restaurants in Lexington. Would definitely book again. Thanks!
    Great setup for several couples visiting Lexington. Three bedrooms have their own bathroom, there is ample hang out space, and its walkable to bars and restaurants. Its a beautiful home! My only warning is that the garage is tiny – we were not comfortable parking anything other than a sedan in the garage space. Also, though it was relatively easy to find street parking, there was minimal street parking on the street the house is on; we had to walk a couple blocks.
    Really nice property with easy access to all that Lexington has to offer. Would definitely book again next time I’m in Lexington.
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    from USD 1,181
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    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.

    Dreaming of Lexington – your dream vacation awaits you
    42 reviews
    Condo
    6 Guests
    3 Bedrooms
    2 Bathrooms
    Top guest reviews
    What an amazing condo! Cannot say enough about it and I would give it more stars if I could. The property was nothing short of outstanding from location to decor to the owners attention to details. I highly recommend that if your are traveling to Lexington, KY or visiting the Bourbon trail that you stay here, you will not be disappointed. Appreciate the owners sharing this gem with us!
    This place is unreal, down to the little details. We had a great time in Lexington and being able to just chill at this place after all of the distillery tours was awesome. We’ll definitely be back!
    We had the best time staying here! Can’t wait to come back! Highly recommend!
    This place really was amazing. Clean, convenient, and comfortable. Having a pizza place, distillery, and three or four bars in walking distance didn’t hurt either. The train in the morning is loud but a small price to pay for an otherwise perfect stay.
    This was one of the best VRBOs I have stayed in. Great place for small gatherings.
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    from USD 400
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    Once you’ve had your fill of bourbon, check out more things to do while in Kentucky:

    • How To Spend An Incredible Weekend In Beautiful Lexington, KY
    • 8 Delicious Restaurants To Try In Louisville, Kentucky
    • 11 Fantastic Things To Do In Beautiful Louisville, Kentucky

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