Holiday rentals in Loretto

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Top-rated holiday rentals in Loretto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

The exterior of the home features a charming white façade with black accents, complemented by a small set of steps leading to the front door. Lush green grass surrounds the property, and a gravel pathway is lined with decorative stones and small shrubs.

Home in Springfield

Bourbon Country Schoolhouse

Enjoy staying in a piece of history within this old one room schoolhouse converted to a two bedroom home. Sit out on the swing or by the firepit as you enjoy peaceful sounds of the country and the creek adjacent to the property. Located right on the Bourbon Trail with only a 5 min drive to Maker’s Mark, 17 min to Limestone, and 20 min to Log Still Distillery. Venture in to the city of Springfield to learn about Abe Lincoln and his parents, married in the courthouse, still being used to this day!

FamilyLocationAccess

4.98 out of 5 average rating, 158 reviews

Top guest favourite

Home in Loretto

Off The Mark

Located in the scenic countryside of central KY—In the middle of nowhere, minutes from everywhere (including Makers Mark) Close to: historical sites, Lincoln’s country, distilleries, oldest Catholic parish this side of the Allegheny Mtns, the Abbey of Gethsemani-Trappist/Cistercian monastery famous for fruitcake, fudge & Thomas Merton We can also host wedding guests for the many local venues. Outdoor adventures/hiking is never far away. Beautiful views and comfy beds await after days exploring.

LocationFamilySleep quality

4.96 out of 5 average rating, 28 reviews

Top guest favourite

A tiny house on wheels is illuminated at night, revealing a warm glow from its windows. Surrounding lights cast soft radiance on the grassy area, complementing the inviting fire pit nearby, where smoke gently rises against the backdrop of the starry sky.

Tiny home in Loretto

Shot Glass Tiny House, 3 miles to Maker’s Mark

🏆 Featured as one of “5 Unique Stays in Marion County, Kentucky”, January 30, 2026. This is glamping at its best! Stay under the stars at the Shot Glass Tiny House on wheels, tucked at the end of a quiet backroad on the bourbon trail just 3 miles from Maker’s Mark. Enjoy rustic comfort while observing wildlife through the large front picture window and surrounding windows. Explore the Bourbon Trail by day, then return to relax by the fire pit, gazing at the stars in this cozy nature retreat.

ValueLocationTV

5.0 out of 5 average rating, 222 reviews

Guest favourite

A modern house is surrounded by lush greenery and elevated above a scenic landscape, offering expansive views of rolling hills and open fields. A gravel driveway leads to the home, which features a single-story design with a dark roof and light-colored walls.

Home in Raywick

The Ridge- Views, Hot Tub, Privacy & Relaxation

The Ridge is a scenic retreat nestled on a picturesque hillside in Kentucky’s famed Bourbon Trail region! This charming home is the perfect backdrop for a relaxing getaway. Unwind on the expansive deck, perfect for sipping your morning coffee or enjoying a glass of bourbon in the hot tub as the sun sets. Situated right on the Bourbon Trail, you’re just minutes away from some of Kentucky’s most renowned distilleries. Explore the rich heritage of bourbon, making with nearby tours and tastings.

LocationValueGrill

4.95 out of 5 average rating, 59 reviews

Top guest favourite

Home in Springfield

Fall Bourbon Escape | Hot Tub + Fire Pit

Explore 10+ distilleries from one Bourbon home base in Kentucky! The Kentucky Barrel House is an upscale boutique retreat perfectly positioned between Maker's Mark & Bardstown. Soak in the private hot tub, enjoy the fire pit, or walk downtown for dining. Full kitchen, large fenced yard & pet friendly. NEW Potter Jane 3.2 mi, Limestone Branch/Yellowstone 8 mi, Maker's Mark 10 mi & Bardstown Distilleries including; Lux Row, Heaven Hill, Bardstown Bourbon Co. Custom itinerary included!

LocationFamilyBathroom

4.99 out of 5 average rating, 120 reviews

Top guest favourite

A comfortable living area features a brown leather sofa adorned with plaid cushions, accompanied by a light-colored armchair. A round coffee table rests on a patterned rug, displaying magazines. Indoor plants and a decorative lamp add a touch of greenery and light to the space.

Farm stay in Loretto

The Barrel Head

* LOCATED RIGHT ON THE BOURBON TRAIL * At the Barrel Head bed, we strive to make our guest feel as comfortable as possible. This location has been newly remodeled and furnished; a brand new queen size bed, pull out sofa, and coffee bar ensure that you are getting the sleep and energy you need for all of your endeavors while staying on the Bourbon Trail. The Barrel Head is also handicap accessible. There are not any steps, and we have installed a walk in shower for anyone in a wheel chair.

ValueLocationSleep quality

4.99 out of 5 average rating, 520 reviews

Top guest favourite

A vibrant sunset casts shades of orange and pink across the sky, illuminating the spacious property. A gravel driveway leads up to a barn structure, flanked by green grass and a small gazebo. Silhouettes of trees are visible in the background.

Farm stay in Loretto

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

LocationFamilyWalkability

4.98 out of 5 average rating, 133 reviews

Top guest favourite

A serene view is captured of a wooden bridge extending over a calm body of water, with a cabin visible in the background. Surrounding trees reflect in the water, enhancing the natural beauty of the space. A second pavilion is seen to the right.

Cabin in Lebanon

*NEW* Secluded Cabin On Private Lake

Woodland Acres is located in the Heart of Kentucky, with spectacular views all around, year-round! Come enjoy this piece of heaven right on the Bourbon Trail! This unique and spacious hideaway has breathtaking views and is situated just 7 minutes from downtown Lebanon, KY. Enjoy a private lake and fishing dock, take a hike through the vegetation that surrounds you, or enjoy a cup of coffee on the wraparound porch. Ideal for leisure seekers, nature lovers, and families alike!

FamilyLocationGrill

5.0 out of 5 average rating, 70 reviews

Top guest favourite

An aerial view captures the property surrounded by lush farmland. The layout includes a swimming pool and neighboring structures, featuring manicured lawns and ample greenery. A winding driveway leads through the landscape, emphasizing the spaciousness of the 72-acre setting.

Farm stay in Raywick

Missy’s unique stays on the bourbon trail .

Welcome to this funky and eccentric property that sits on 72 acres of luscious farmland in the heart of Kentucky, situated along the bourbon trail .. Previously “Missy’s café ) now turned it into a country getaway for family, Friends or sweethearts .. it is set up for intimate events (extra) or just a nice quiet stay .. it has a beautiful view of the farm and surrounding knobs.. not to far away from civilization, but far enough too get away and enjoy nature

ValueLocationCleanliness

4.97 out of 5 average rating, 152 reviews

Superhost

Home in Bardstown

The Bourbon Trail Retreat

Welcome to The Bourbon Trail Retreat! Escape to peaceful Kentucky just minutes from Bardstown and the Bourbon Trail. This spacious barndominium blends modern comfort with rustic charm, perfect for bourbon tours, family vacations, couples, or weekend getaways. Enjoy a full kitchen, cozy bedrooms, fast Wi-Fi, scenic farm views, and easy access to local dining, shopping, parks, and attractions. Relax, unwind, and make lasting memories.

LocationHot tubKitchen

4.67 out of 5 average rating, 3 reviews

Top guest favourite

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. A textured brick wall features a decorative mural highlighting bourbon and moonshine. The granite countertop is complemented by a stainless steel sink and overhead pendant lighting, creating a functional and inviting cooking space.

Guest suite in Lebanon

Spirit on Main

Welcome to Spirit on Main, located in Lebanon, the heart of Kentucky. Located on Main Street, in the middle of all of the local activities, Spirit on Main is prime location for visiting your favorite bourbon spots! Whether you are in town for a couple’s getaway, trip with friends or on business, Spirit on Main will be your home away from home in the beautiful small town of Lebanon.

FamilyLocationTV

4.95 out of 5 average rating, 214 reviews

Top guest favourite

A small outdoor deck features a red metal bistro table accompanied by two matching chairs. Atop the table sits a bright red planter filled with yellow flowers, surrounded by lush greenery in the background.

Flat in Lebanon

Deep on the Bourbon Trail

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.

LocationValueCheck-in

4.94 out of 5 average rating, 131 reviews