Vacation rentals with outdoor seating in Shepherdsville

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Top-rated outdoor seating rentals in Shepherdsville

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Cabin in Lawrenceburg

4.99 out of 5 average rating, 170 reviews

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Top guest favorite

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

4.98 out of 5 average rating, 111 reviews

Bourbon Trail 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!

Top guest favorite

A cozy bedroom features a spacious bed with crisp white linens and decorative pillows. Above the bed, a vibrant artwork of a cow adds a touch of character to the room. A bedside lamp and a small blue nightstand provide additional comfort.

Place to stay in Vine Grove

4.99 out of 5 average rating, 138 reviews

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

Top guest favorite

A comfortable living area features a soft beige couch and a matching armchair positioned around a dark wood coffee table. A plush area rug enhances the warmth of the wood flooring. A workspace with a desk and lighting can be seen in the background.

Apartment in Radcliff

4.99 out of 5 average rating, 110 reviews

Blue Moose Studio 7 miles from KNOX, 9 to E-town

Comfy studio / Private Entrance, 7 miles from Knox / 9.6 to E-town Sports Complex. Situated one mile off the main road on a dead end, equals a quiet relaxing stay. Work remotely? We got you! How about an external monitor, printer and spacious desk? If you're here for activities at the Elizabethtown Sports Complex, Headed to the Bourbon Trail, or checking out the area before a move, it's a great choice! NO Pets or Smoking! Your host is located on site and will be happy to assist you.

Top guest favorite

A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

Home in Fern Creek

4.99 out of 5 average rating, 194 reviews

"Call Me Old-Fashioned" in Derby & Bourbon Country

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!!

Top guest favorite

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

5 out of 5 average rating, 234 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite

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

4.99 out of 5 average rating, 482 reviews

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.

Top guest favorite

A wooden deck leads to the entrance of the cottage, surrounded by lush greenery. A concrete patio features a circular table with benches, providing a shaded outdoor space. The natural setting creates a serene environment, with trees framing the view.

Cottage in Hodgenville

4.98 out of 5 average rating, 218 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

Guest favorite

A spacious sleeping area features a king bed with a soft beige quilt and matching pillows. Two bedside lamps provide warm lighting beside wooden nightstands. The ceiling is accented by textured panels, and the cozy carpet extends across the floor.

Place to stay in Shepherdsville

4.88 out of 5 average rating, 306 reviews

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

Top guest favorite

A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.

Guesthouse in Germantown

4.96 out of 5 average rating, 235 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Top guest favorite

A cozy living area is furnished with a spacious sectional couch and a leather armchair. A wooden coffee table holds magazines. Light-colored walls are complemented by framed artwork, and a pass-through window connects to the kitchenette area.

Guest suite in Coxs Creek

4.99 out of 5 average rating, 209 reviews

★Jenny's Place - Basement Suite, Private Entrance★

Welcome to Kentucky & Bourbon Country! Jenny's Place includes your own private lower-level walkout suite, with all the amenities, nestled in a quiet subdivision. We are centrally located near many events and activities, including the Bourbon Trail, Four Roses Bottling (5 min away), Jim Beam Distillery (10 min away) and Bernheim Forest (10 min away). We are conveniently located 15 minutes from Bardstown, the Most Beautiful Small Town in America. Come see us!

Guest favorite

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

4.96 out of 5 average rating, 145 reviews

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS