Holiday houses in Simpsonville

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Top-rated holiday rentals in Simpsonville

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

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Top Guest favourite

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

4.98 out of 5 average rating, 254 reviews

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

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)

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Top Guest favourite

A spacious studio apartment is showcased with a comfortable bed adorned in a black and white checkered pattern, complemented by red accents. A cozy seating area features a light-colored sofa. Natural light illuminates the wood flooring, and decorative elements enhance the inviting layout.

Apartment in Simpsonville

4.98 out of 5 average rating, 141 reviews

Ridgecrest Estate. Comfort and Convenience.

Enjoy the best of Kentucky in our immaculate, 650-sq-ft. upstairs studio apartment with private entrance on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate offers a quiet, peaceful environment in the heart of the Bourbon Trail. Quick access to I-64 (1/2 mile), 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. Sleeps two. No children under 13. Pool access not included with reservation.

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Top Guest favourite

A charming single-level home is presented with a welcoming front porch featuring rocking chairs. Lush grass and neat landscaping frame the stone pathway leading to the front door. Trees provide shade, creating a serene setting in a quiet neighborhood.

Home in Shelbyville

5.0 out of 5 average rating, 64 reviews

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville. Start your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! A short drive to Louisville, Lexington, Frankfort, KY Derby and PGA Championship 2024 @ Valhalla! Sleeps 6

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Top Guest favourite

A hot tub is situated under an awning, surrounded by soft, white curtains that provide privacy. The bubbling water reflects the greenery of trees beyond, enhancing the serene atmosphere of the outdoor area.

Cottage in Simpsonville

5.0 out of 5 average rating, 66 reviews

KY Cottage near Bourbon, Expo & Horse Park|Hot Tub

Welcome to Miles Around KY Cottage with a relaxing hot tub! Your cozy "Goldilocks" home base,perfectly placed for exploring! Easy drives to Louisville, Frankfort, Bardstown Lexington and more. Shopping: Outlets just 1 mile away! Parking: 4 cars and up to 20ft trailers -message us . Note: We are building our dream home 1/2 acre away, far enough to keep your privacy, but we do share the driveway. Children welcome at your discretion- home is not baby proofed. See house rules for more info.

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Top Guest favourite

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

4.98 out of 5 average rating, 312 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.

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Guest favourite

A single-story home with a welcoming front porch is surrounded by well-maintained lawns and shrubs. The structure features multiple windows and a gabled roof, with warm evening light illuminating the exterior. A paved path leads to the entrance, enhancing accessibility.

Home in Simpsonville

4.98 out of 5 average rating, 40 reviews

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

Welcome to the Haven in the heart of Simpsonville, KY, the Saddlebred capital of the world. Located within walking distant of local eateries, shopping, & coffee. The Haven is close to local Distilleries, centrally located between Louisville and Lexington, on the Bourbon Trail, and less than 2 miles from The Outlet Shoppes of the Bluegrass. This spacious 3 bedroom, 3 bath home was designed to be a place of peace & comfort and is perfect for both families and group trips alike.

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Top Guest favourite

A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 145 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

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Top Guest favourite

A two-story guest house is situated amid lush green grass and shade trees. The exterior features a combination of light siding and dark accents, with a covered porch furnished with chairs. Windows allow natural light to engage the interior, enhancing the peaceful rural setting.

Farm stay in Shelbyville

4.98 out of 5 average rating, 57 reviews

Annola Farm Guest House

Stay and be delighted with this newly renovated two-story guest house which adjoins our 11-stall horse barn. Framed by covered porches and shade trees, our guest house is a wonderful place to unwind and relax during your stay in beautiful central Kentucky. The best of both worlds--a lovely rural setting situated only minutes from the interstate, making travel to Churchill Downs, Valhalla Golf Course, and other attractions in nearby Louisville and Frankfort a breeze.

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Top Guest favourite

Dome in Mount Washington

4.98 out of 5 average rating, 257 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

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Top Guest favourite

A newly renovated cottage is featured with a dark blue exterior and wooden accents. The façade includes large windows adorned with shutters, while a gravel driveway extends toward the entrance. A gently sloping landscape with greenery is visible in the background.

Cabin in Mount Eden

4.97 out of 5 average rating, 188 reviews

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

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Guest favourite

The spacious living area features a large gray sectional sofa arranged comfortably on a soft area rug. A rustic coffee table sits at the center, surrounded by books and decor. A custom bookshelf is filled with various items and framed photos, complementing the exposed wooden beams overhead.

Loft in Shelbyville

4.99 out of 5 average rating, 142 reviews

Sleeps 16/near everything-Transportation available

"The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably cohabitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave." - Bourbon Review Magazine

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Guest favourite

An outdoor fire pit area is surrounded by Adirondack chairs arranged in a circular pattern. Warm string lights hang overhead, illuminating the space, while the house stands in the background against a vibrant sunset sky.

Home in Pewee Valley

4.95 out of 5 average rating, 205 reviews

Bourbon Trail*Tesla EV charger* HOT TUB

Welcome to the Bourbon Bungalow, a tastefully restored farmhouse on the famous Kentucky Bourbon Trail. This southern retreat is on the outskirts of Louisville in the quaint city of Pewee Valley. A short drive to some of the states most sought after locations such as Churchill Downs, bourbon distilleries, horse parks, caves, Shelbyville, Bardstown, & more! The Bourbon trail is waiting for you!

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