Holiday houses in Hebron Estates

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Top-rated holiday rentals in Hebron Estates

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

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Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 260 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm 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 bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

2–9 Sep

$309 NZD per night

Guest favourite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 180 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

9–16 Jul

$226 NZD per night

Guest favourite

Guest suite in Louisville

4.98 out of 5 average rating, 179 reviews

Spacious Lower-Level in Quiet Neighborhood

This is a spacious, walk-out lower level with a private entrance. Our quiet neighborhood is 1 1/2 miles from I-265, which means easy access to Louisville or beyond the city to bourbon country. It has a large living area and a fully equipped kitchen. Adventure lovers will like being 5 miles from The Parklands. Downtown Louisville is 20 minutes away. The space has 1 queen bed, 1 double bed, and twin bunk beds. It sleeps 5-6 comfortably. We live upstairs so we are available if needed.

7–14 Aug

$264 NZD per night

Guest favourite

Cottage in Hodgenville

4.98 out of 5 average rating, 141 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.

7–14 Feb

$167 NZD per night

Guest favourite

Tiny home in Shepherdsville

4.95 out of 5 average rating, 210 reviews

Cozy Tiny House Near Louisville

The tiny house is 200 square feet, but has everything you need for a cozy stay! It’s located inside our half acre fenced in backyard which is right off I65 and 15 minutes to downtown Louisville. Fast food, restaurants, gas stations, and laundry mat are less than a mile away. The backyard is a shared space with us, so there’s a small chance you may see us out there. We built the tiny house ourselves. We take pride in it and hope you choose to experience tiny house living!

25 Jun – 2 Jul

$198 NZD per night

Guest favourite

Guest suite in Coxs Creek

4.98 out of 5 average rating, 184 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!

8–15 Jul

$186 NZD per night

Guest favourite

Cabin in Elizabethtown

4.91 out of 5 average rating, 196 reviews

The Cabin- private & cozy 1 queen bed 1 bath

Take a break and unwind at this peaceful oasis. Blurring the lines between structure and nature, this cabin retreat inspires a feeling of tranquility. The footprint compacts everything one could need- living, kitchen, bed, bathroom, washer/dryer, games and more. Enjoy the peaceful sounds of nature while napping in the hammock. Cook dinner over an open flame in the firepit. Test your skills to beat the high score on PacMan arcade or the foosball table.

16–23 Oct

$211 NZD per night

Guest favourite

Loft in Shepherdsville

4.88 out of 5 average rating, 238 reviews

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and a short drive to Mammoth Cave 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.

6–13 Jan

$161 NZD per night

Guest favourite

Home in Louisville

4.88 out of 5 average rating, 78 reviews

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!

1–8 Jul

$227 NZD per night

Guest favourite

Cottage in Louisville

4.95 out of 5 average rating, 148 reviews

2 BD 1 BA Serene Setting Retreat House

Carriage home is located on beautiful Arnoldtown Rd. 15 min. from Churchill Downs and 20 min. from downtown Lou. We are 15 minutes from Freedom Hall or the Fairgrounds and 22 miles from Fort Knox. It sits in a natural setting on 5 beautifully landscaped acres. There is a large parking area for those who may need to bring a trailer. Bathroom and bedrooms are on the 2nd floor. Peaceful..in a rural setting but inside the city.

9–16 Sep

$263 NZD per night

Guest favourite

Apartment in Mount Washington

4.94 out of 5 average rating, 173 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

15–22 Oct

$185 NZD per night

Guest favourite

Home in Bardstown

4.95 out of 5 average rating, 459 reviews

Creekview Farm: Bourbon, Horses, and Sunsets

On this beautiful 19 acre horse farm, you will enjoy beautiful sunrises and sunsets. You will have the country feel while only being 3.5 miles from downtown Bardstown. The airbnb apartment located in the front of the horse barn. It is located behind the main farm house which is a long term rental house. The horses, cats, goats, chickens, and dogs belong to the long term rental tenants.

31 Aug – 7 Sep

$251 NZD per night