Airbnb & Vacation Rentals

Arbuckle Creek Retreat

Arbuckle Creek Retreat - Rental in Lebanon Kentucky

Arbuckle Creek Rd. Lebanon, KY 40033

Link to Airbnb Here

This four bedroom/3 bath Lincoln Log-style cabin amongst the hills of Lebanon, Ky was built in 2006 and sits on 55 acres. Fully equipped with scenic 360 views and modern comforts for a relaxing weekend away… It only needs you! ACR is a true escape from the city. Located up a quarter mile private gravel drive, a secluded, wooded lot. Just you and the wildlife. It’s newly remodeled and furnished with love & relaxation in mind for you to enjoy. 

Arbuckle Creek Retreat has been everyone’s favorite place to gather for family reunions, birthdays, holiday visits or vacations. So much life and good times have been lived in this cabin. The ultimate favorite place to hang out at the cabin is the front porch. Nothing beats starting the day watching a sunrise from the front porch with a hot cup of coffee or tea. The colors are beyond description and they change constantly till the sun tops the distant ridge. 

From the front porch you could watch a rain shower come over the distant ridge, roll down into the valley, and as the rain moved across the valley, the far off ridge would clear. You could watch the rain come across the valley, right up the cabin’s hill and pass right on over it. Nature is on full display from this front porch. 

If the sun is too warm on the front porch, the large screened back porch is the second best place this cabin has to offer. This screened porch looks onto acres of woods where many hours have been spent visiting with family and friends, talking about what is happening in the family or the news, taking naps on the daybed, eating so many meals, and just reading a book. Though the inside of the cabin is wonderful, nothing beats the porches and views of this lovely cabin.

The Bourbon Trail Landing

Airbnb Here

The cottage is on a farm that was purchased by Brandon’s great great grandparents in 1917 for $1800 and has been in the family ever since. It is nestled in the trees next to a pond. Here you will potentially see cranes, deer, hawks, a German Shepard named Lacy and her Great Dane friend Charlie who live up the road in the main house and love to greet our visitors. The property has an 1119 foot landing strip for anyone who wants to fly a small plane in and park it in the field during their stay.

Studio cottage with a queen bed, couch and wifi.
Full bathroom with a stand up shower.
Kitchen has a small fridge with freezer, microwave and a stove.
Very quiet and private setting
Outdoor gas fire pit

3 guests1 bed1 bath

The Baker House

Airbnb Here

Downtown, close to everything Great location. Big backyard, lots of parking.
Guest have access to backyard front yard
This is apartment is an Airbnb on bottom floor. There are 2 apartments 2 upstairs 2 downstairs

4 guests2 beds1 bath

The Coletta House


Raywick, KY 40060

Phone (859) 619-5052

Link to Airbnb Here

The Coletta House is a quaint country home with tons of charm. It sits along the bourbon trail and is within 15 miles of several distilleries. The area is known for its re recreational activities, such as hunting, kayaking and atv riding. It has been the home of the Bickett family for Many years, and Coletta is the Mama of 2 of the Cornbread Mafia boys. The home itself features stories from the family including letters from Johnny Boone.


The home has been restored to reflect the times when the Bickett family lived there and the many trials and tribulations and celebrations they went through.
The area is also known for Ham Days, Bourbon Trail, Jet Universe, kayak Ramp is 2 houses down, Yellowstone Distillery, Missy’s Out of the Way Café, Riley Christmas light display, Maker’s Mark, Jester’s Distillery, Scott’s Ridge (5 minutes down the road) Shit Creek (little Cades Cove), Green River, My Old Kentucky Home, fishing, hunting and kayaking.


Entire home with exception of storage room

Country Cottage

Country Cottage - Rental in Lebanon Kentucky

1280 Mannsville Rd. Bradfordsville, KY 40009

Phone (859) 619-5052

Link to Airbnb Here

This cozy cottage is located on a beautiful farm filled with warmth and charm. If you are looking to get away and enjoy peace and quiet you have found the place. Come and relax in the country. Find yourself in the middle of the bourbon trail on a beautiful 2500 acre farm surrounded by knob land and rolling pastures.

Take a hike on one of the many trails right outside your door. Trek the bourbon trail, historic churches and landmarks of Lebanon. You may just want to relax and enjoy farm living at its best. What ever you want you will find it here on the farm. Lebanon is 7 miles away with Makers Mark, KY cooperage, Limestone Branch, shops, and restaurant

Cozy Ranch

Cozy Ranch - Rental in Lebanon Kentucky

166 Cemetery Rd. Lebanon, KY 40033

Phone (270) 402-7824

3 bedroom 1 and a half bath house. For more info or to book this property check out their Airbnb Page here.

Deep on the Bourbon Trail


Link to Airbnb Page

Deep on the Bourbon Trail is a newly renovated upstairs apartment with a private entrance over a detached garage. Located on the main thoroughfare as you come into the quaint city of Lebanon. The apartment is within walking distance to wedding venues, historic landmarks, and our community theater.

Deep on the Bourbon Trail has a private deck where you can enjoy sunsets.
We are located within one mile of Rosewood Golf Course, Limestone Distillery, and Independent Stave where you can have tours.

The apartment is over my garage and you will have to climb 14 steps which are behind the garage.

Distilled Quarters

Lebanon, KY 40033

Link to Airbnb Page

Enjoy some of Kentucky’s best views of farm life in this cozy oasis perfect for any occasion. Surrounded by several acres and a large creek perfect for exploring! The Distilled Quarters is located directly on the bourbon trail only a quick 5 minute drive to Maker’s Mark distillery and Jester’s Winery.

Downtown Abode

Downtown Abode - Rental in Lebanon Kentucky

222 West Mulberry Street Lebanon, KY 40033

Phone (270) 692-7217 or (270) 692-8650

Link to Airbnb Page

Beautiful rental home in downtown Lebanon, and a prime location for visiting many locations on the Bourbon Trail or the Lincoln Heritage Trail. 60 miles from Louisville or Lexington and only 15 miles from Historic Makers Mark Distillery.

Just like home. This is what a lot of our guest have described their stay at the downtown abode. Imagine after a long day of travel and enjoying the Bourbon Trail ; you come home and have steaks cooking on the grill and potatoes cooking in the oven. The ladies sitting around the dining room table sipping on a glass of wine and the men sitting in comfortable recliners sipping on their favorite bourbon and watching a ballgame on TV. 

With the open concept floor plan everyone is together and enjoying each other‘s company. When it’s time to go to bed you can snuggle with your loved one in a large comfortable bed. What more could you ask for?

Empire Estate

418 N Spalding Ave., Lebanon, Kentucky 40033

(270) 692-9777

Airbnb Here

Enjoy all the amenities of Empire Estate in Ticky’s Cottage, such as an inground pool, 3.5 manicured acres to roam on, regulation sand volleyball/badminton court, fire pit next to a stream, horseshoes and more. All this is located within 50 minutes of all major distilleries on the Kentucky Bourbon Trail. This is a genuine Bourbon Country getaway spot for comfort and serenity but plenty of fun just minutes away. The proprietor knows the area and all the ‘can’t miss’ activities and sights.


Plenty of room and comfort is on tap here. Bedrooms are on opposite ends of the cottage and there’s plenty of free parking on pavement. Sit a spell on the multi-level deck just a few steps away from your front door or grab a rocker on The Porch in front of The Big House.


Empire Estate is located right on Spalding Avenue, the grand entrance to Lebanon, Kentucky! Downtown and other sights and attractions are not only close but super easy to find, such as Maker’s Mark Distillery, Limestone Branch, Jester’s Winery, Rosewood Golf Course, Sister of Loretto Motherhouse campus, Lincoln Homestead State Park, Green River State Park, Log Still Distillery (big-time concerts often) and My Old Kentucky Home State Park.


Your comfort and enjoyment is the priority at Empire Estate. A coded lock provides easy check-in. The proprietor is accessible and knowledgeable of the area and what’s going on during your stay.

The Fannie Brown

119 West High Street, Lebanon, Kentucky 40033

(270) 692-6945

Airbnb Here

  • 4 Bedrooms – 2 Queen, 1 Full and 1 Twin
  • 2 and 1/2 Baths
  • The master suite offers a queen bed and full bath
  • Large living room, Dining Room, and Den all on the first floor
  • Fully equipped modern kitchen
  • Outside Private Patio with seating for 8 and Gas Grill
  • Washer/Dryer 

The Farmhouse

The Farmhouse - Rental in Lebanon Kentucky

2355 Barbers Mill Rd. Lebanon, KY 40033

Phone (270) 692-7776

Link to Airbnb Page

This home is on a 3rd generation family farm. The decor is all country related and most is original to the house. It was a dairy farm until recently, but now they raise beef cattle which you can see grazing from the front or back porch. It’s still actively worked so you see someone on a tractor doing something almost every day. 

Lebanon is located in the heart of KY and within 30 minutes of various distilleries along the Bourbon Trail. This location is 15 minutes from the famous Maker’s Mark Distillery and only 5-10 minutes from Limestone Branch Distillery.


Forest St.

309 N. Forest St.  Lebanon, KY 40033

Link to Airbnb Page

Enjoy this 3 bedroom & 1.5 bathroom right in the middle of Lebanon KY! This property holds a large fenced in backyard suitable for your family or friends! This home can sleep 6 people in our bedrooms but can sleep 1-2 more on our sofa bed! The driveway will hold multiple cars.
This space has a large living room with a TV. On the main level is a half bath, bedroom, kitchen and dining room table (sits up to 6 people.) The upstairs has 2 bedrooms (both kings) and a full bath.
The driveway will hold multiple cars, but parking on the street in front of the house is allowed!
The fridge does not have an ice machine.
There are neighbors on both side of the house.
The washer & dryer is located downstairs in the basement

The Heart of Downtown

137 East Main St. Lebanon, KY

137 East Main Street, Lebanon Ky. Home of our completed Airbnb. Enjoy all the amenities of this 2 bedroom, 1 bath rental with all the conveniences of downtown. Lots of places close to walk and explore. We are in the mix of the bourbon trail as well. You will experience the small town comfort, relaxation and beauty with good food, entertainment and of course the best bourbon in the USA, all within 1-50 miles of this rental.
The Federal Building was built in 1830 and has been well maintained and modernized. It will have the feeling of stepping back in time. We can be reached at 812-322-8143 or 270-402-7809.

Greenhaven Farm

Fogle Rd. Loretto, KY 40037

Airbnb Here

Greenhaven Farm features a cozy and rustic farmhouse on 58 scenic acres. This serene getaway (which has been in the Green family for over 75 years) allows you to escape outside distractions while still staying within 15-20 minutes of Lebanon and several of the country’s top bourbon producers.

The farm allows guests the flexibility of an intimate visit while still offering enough space to entertain a small group. The farmhouse has 2 bedrooms with queen-size beds in addition to a sleeping loft with a full size bed plus 2 twin beds. The eat-in kitchen offers all of the modern conveniences — stove, microwave, dishwasher and refrigerator. The spacious bathroom has lots of room with a separate shower and garden tub. For outside enjoyment, the back deck, gas grill and fire pit are all available for guests to use.

The Hourglass

The Hourglass - Rental in Lebanon Kentucky

421 West Main Street Lebanon, KY 40033

Phone (270) 402-1135

Link to Airbnb Page

Enjoy your stay in this stunning 160 year old home. You can admire and appreciate the Italianate architecture while having the comfort of modern amenities. Located in the heart of Kentucky,  this place is perfect for families, couples or individuals on business.

The first level has a kitchen, laundry room, sunroom with a daybed and trundle bed, dining room and full bath. The second level has another full bath. The third level has a great room with a futon and a sofa and 2 guest rooms with full beds.
The front lower level of the house is used as a wedding business and is closed off to guests. This business is open by appointment only and it is rare to be there at the same time as guests. If you would like a tour of the remaining space please just let them know and they are happy to let you in and show you around!


Knott on Main

Knott on Main - rental in Lebanon Kentucky

319 S. Proctor Knott Ave. Lebanon, KY 40033

Visit AirBnB Listing Here

Phone (270) 402-3958

Knott on Main is a beautiful, historic home for rent in the Heart of Kentucky. This is the perfect spot for a trip with friends, wedding parties or even business trips. 

This location is packed with all the best amenities, including: Three bedrooms, 2 bathrooms, Game Room, Full Kitchen, All stainless steel appliances, Flat Screen TV’s in the living room and in the game room, Washer and Dryer, Free Wifi. The location is within walking distance of Main Street in Lebanon as well as the beautiful Graham Memorial Park. 

Lebanon Suites

Lebanon Suites - Rental in Lebanon Kentucky

255 W. Main Street Lebanon, KY 40033

Phone (270) 692-6663 or (859) 481-1073

Located in the heart of historic downtown Lebanon. This establishment has everything you need for a pleasant and comfortable stay. While staying there take a stroll Main Street to visit local businesses for dining and shopping and entertainment. If bourbon is your thing, this airbnb is in the heart of the Bourbon Trail. Maker’s Mark, Limestone Branch and Kentucky Cooperage are all just a short drive away.

Here at this home-away-from-home you will find great amenities such as king size bedrooms, large dens with vaulted ceilings, fully equipped kitchens. Free Wi-Fi, washer and dryer, televisions, and fitness center with sauna and tanning beds located downstairs.

The Little Red Cabin

Helm Schoolhouse Rd. Lebanon, KY
Airbnb Here

A little red cabin on 20 acres with lots of wild life. This is a great place to get away too. location is 5 miles from Lebanon. The cabin has a open concept, full kitchen & bath with a stand up shower. The loft has a queen size bed. Equipped with all the standard amenities.

Missy's Unique Stay

860 Horseshoe Bend Rd. Raywick KY 40060
Airbnb Here

It is an actual café that has been turned into a unique overnight stay and a great place to host gatherings and events .. it also remains a private flea market with things for guest to purchase is located near the bourbon trail .. Makers Mark , Yellowstone and the new and upcoming log still distillery is all within 10 miles of this unique space .. The rolling fork also rolls around this property like a horseshoe.. so kayakers take note..the get in and get out access points are both within 5 miles with easily accessible parking .. located in the back you will find a beautiful deck , equipped with a grill, fire pit and a great view for birdwatching.

8 Guests 2 Bedroom 1.5 Baths

Modern Barn Loft

This unique, studio apartment is located in the heart of Kentucky, right on the Kentucky Bourbon Trail, where you can fully experience the beautiful, country scenery while also enjoying the convenient location with everything you will need just minutes away for your stay at the Marion Barn.
-Fast WiFi
-YouTube TV
-Modern, studio style, newly renovated barn lofts
-Fully furnished (washer, dryer, stove, microwave, refrigerator)
-Just outside the city limits of Lebanon, KY
4 guests 2 beds 1 bath

The Olde Farmhouse

367 Ed Cecil Rd. Raywick, KY 40060

Phone (270) 699-0779

Airbnb Here

The Olde Farmhouse is secluded on 5.8 acres and is on the historic Bourbon Trail. The house has a master on the main floor with a queen bed connected to the bathroom. There is an upstairs sleeping space that accommodates one queen bed and two twin beds. Beautiful wrap around porch for your morning coffee enjoyment or evening relaxation. 

All that can be heard on this property are crickets and frogs with lovely sunsets. The farmhouse is within driving distance of several wonderful sights and activities. There are many distilleries to tour as well as Mammoth Caves, Green River Lake, Lincoln’s Birthplace and childhood home plus many more activities as listed in a notebook on property.

Perfect Get Away

Perfect Getaway - Rental in Lebanon Kentucky

645 Marlowe Ln. Bradfordsville, KY 40009

Phone (859) 619-5052

Link to Airbnb Here

You are in the middle of a 2500 acre farm surrounded by knob woodland. A perfect get away for family and friends. Wide open space with no neighbors except wildlife. Cross a very small creek and onto a gravel driveway to get to your “tucked away” retreat. Sit by the fire pit and enjoy star gazing. Come explore farm living at its best.Imagine yourself sitting on the porch with your cup of coffee looking out at white tail deer grazing in the morning. 

Take a hike on one of the many trails right outside your door. Trek the bourbon trail, historic churches and landmarks of Lebanon. You may just want to relax and enjoy farm living at its best. What ever you want you will find it here on the farm. Lebanon is 7 miles away with Makers Mark, KY cooperage, Limestone Branch, shops, and restaurants. 

Spirit on Main

Spirit on Main - Rental in Lebanon Kentucky

101 ½ W. Main St. Lebanon, KY 40033

Book Here

Phone (270) 402-3958

Located on Main Street, Spirit on Main is a rental in the heart of downtown Lebanon. The location is in the middle of all the downtown shopping, dining and local activities. This is also the prime location for visiting all of your favorite bourbon spots. Whether it’s a couples getaway, trip with friends or business-related, Spirit on Main will be your home away from home.

This spacious suite for up to 6 people includes full kitchen, stainless steel appliances, washer and dryer, free Wi-Fi, flat screen television. When booking with Spirit on Main you will receive complimentary breakfast certificates to local restaurants as well as complimentary tickets to a tour of the Kentucky Cooperage.

Sunny Side Saloon

Airbnb Here

Sunny Side  is a vacation rental on the second floor of Sunny Side Saloon, a historic building that served as a Union Army Commissary during the Civil War and later a local watering hole called Sunny Side Saloon. Sunny Side is located in downtown Lebanon in the heart of Kentucky on the historic Bourbon Trail, just steps from restaurants and the farmer’s market (Wed./Sat. mornings). For more information check out our website, **Interior images are renderings**

Guest access
Sunny Side  has a private exterior entrance and you will have access to the entire space.

5 guests1 bedroom3 beds1 bath

Take A Shot

Airbnb Here

Completely renovated with custom cabinets & granite countertops! Cozy 3 bedroom, 1.5 bath with new kitchen and laundry room with full-sized washer & dryer on the Bourbon Trail! Conveniently located 9 miles from Markers Mark Distillery, 1.5 miles from Limestone Branch Distillery and close to Lebanon’s historic downtown/ Spring View hospital. Now complete & ready for guests. Perfect for a evening of relaxing with friends (cheers!) or to rest after a long days work (or golf)! Come stay awhile!

Nice back patio with table and chairs for 4 for evening meals outdoors with a large back patio and lawn for outdoor activities. Here you can have your Bourbon and drink it too!

Entire home, front back & side lawns with paved front & large back patio with outdoor seating.

Must be 21 years of age or older to book this space.

7 guests3 bedrooms3 beds1.5 baths

Til the Rooster Crows Ranch

Til the Rooster Crows - Rental in Lebanon Kentucky

835 Bob Curtis Rd. Bradfordsville, KY 40009

Link to Airbnb Here

Phone (516) 241-7960

Stay at this working farm/homestead, where breakfast is included using farm fresh eggs and seasonal ingredients. Guests have a secluded second floor: private bathroom (if a larger group there are extra guest rooms and bathrooms) Close to the Bourbon Trail, but a quiet country location: Makers Mark, Limestone Branch & Jester Winery only 25 minutes away and 35 minutes for state parks: 20 minute short drive to Lebanon or Perryville, 60 min to Lexington or Louisville, 23 to historic battle of Perryville