Vacation rentals in Waddy

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Top-rated vacation rentals in Waddy

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Top guest favorite
The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.
Home in Frankfort

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

LocationFamilyAmenities

4.99 out of 5 average rating, 135 reviews
Superhost
Home in Waddy

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Welcome to your Bourbon Trail getaway in Waddy, KY- perfectly located near Lawrenceburg, Shelbyville, Frankfort, and Versailles with easy I-64 access. This charming 3-bedroom, 2-ba home features hardwood floors, a fully equipped kitchen, jacuzzi tub, high-speed Wi-Fi, and self check-in. Relax on the front porch rocking chairs, unwind on the new patio, or enjoy breathtaking sunsets. Ideal for families, couples, or remote workers seeking a peaceful Kentucky escape close to horse country. Book now!

ValueFamilyPets

4.67 out of 5 average rating, 58 reviews
Guest favorite
Home in Waddy

Bourbon Trail Estate | Theater, Games & Hot Tub

✨ Escape to The Bourbon Barrel Retreat ✨ Designed for bourbon trail weekends, family gatherings, and group getaways, this modern 6-bedroom retreat sleeps 16 and is built for making memories. Relax in the hot tub after the distilleries, challenge friends in the game room, enjoy movie nights in the private theater, or gather around the firepit. Next door is a cozy farm with horses! Located just minutes from Kentucky's most popular distilleries. 🌟 BOOK YOUR STAY TODAY! 🌟 Please note: No weddings.

LocationValueAccuracy

5.0 out of 5 average rating, 21 reviews
Top guest favorite
A well-equipped kitchen features dark wooden cabinetry and granite countertops. Four barstools with cushioned seats are arranged around a large island. Stainless steel appliances, including a refrigerator and oven, are visible alongside natural light streaming through a window.
Cabin in Frankfort

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

LocationValueIndoor spaces

5.0 out of 5 average rating, 252 reviews
Guest favorite
The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.
Home in Lawrenceburg

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 191 reviews
Top guest favorite
A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.
Farm stay in Frankfort

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

FamilyLocationSleep quality

4.99 out of 5 average rating, 171 reviews
Guest favorite
The living room is furnished with two large leather sofas and a comfortable plush couch, arranged around a central ottoman. Soft lighting is provided by two table lamps, and natural light streams through a large window, partially dressed with sheer curtains.
Home in Frankfort

Heart of the Trails

Relax with the whole family at this New peaceful place to stay. At the Heart of the Trails you are right in the middle of all the bourbon trails & Wineries In Frankfort & min. to Lawrenceburg & Versailles. We are right next to the highway can be at any surrounding towns in a few! You also have Juniper Hills water park with playground barbecueing & golfing. We also have the game farm educational center to visit all the animals & fishing. Also bourbon tours everywhere. All one level home.

LocationValueGrill

4.89 out of 5 average rating, 172 reviews
Top guest favorite
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

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

*NO smoking property (inside or out)* Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, and support your rejuvenation. 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. (Note:18+only)

FamilyValueNearby

4.99 out of 5 average rating, 267 reviews
Top guest favorite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

LocationFamilyTV

4.99 out of 5 average rating, 593 reviews
Top guest favorite
A modern cabin exterior features a welcoming front porch with wooden railings and chairs arranged for relaxation. Steps lead from a gravel path to the entrance. The building's dark exterior contrasts with the clear blue sky and grassy landscape surrounding it.
Cabin in Frankfort

The Bourbon Coop

The Bourbon Coop is arguably the best situated location on the Bourbon Trail! It is a convenient walk or golf cart ride to Whiskey Thief distillery across the street. Situated a quarter of a mile off interstate 64, in between Louisville and Lexington, with a 15 minute drive into the city of Frankfort. The cabin is located on a beautiful, scenic plot of land, shared by the friendly hosts, chickens, ducks and a couple of goats. This is a comfortable, quiet and quaint country experience!

FamilyLocationGrill

4.99 out of 5 average rating, 118 reviews
Top guest favorite
A gravel path leads up to the cabin, surrounded by lush greenery and tall trees. The cabin's exterior features a mix of wood and metal siding, with a deck extending from the entrance, providing a connection to the natural surroundings.
Cabin in Lawrenceburg

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

LocationValueWalkability

4.99 out of 5 average rating, 134 reviews
Top guest favorite
Dome in Mount Washington

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.

FamilyLocationAir conditioning

4.98 out of 5 average rating, 264 reviews

Popular amenities for Waddy vacation rentals