Holiday houses in Pleasureville

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Top-rated holiday rentals in Pleasureville

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Guest favourite

Farm stay in Williamstown

4.99 out of 5 average rating, 378 reviews

Mabel’s Cabin

Rural Retreat Welcome to Simpson Ridge Farm Come stay at our Amish-built cabin, nestled on a 3rd generation family-owned farm, in the heart of the pastoral Kentucky bluegrass. Take in the tranquil views on the front porch or back deck, as your surrounded by God's creations. This 420 sq. ft cozy retreat offers a comfortable queen size bed, full bath with walk-in shower, WiFi, and an equipped kitchen. Convenient location minutes from The Ark Encounter, Exit 154 on I-75 in Williamstown, Ky.

24–31 Oct

$242 NZD per night

Guest favourite

Home in Stamping Ground

4.97 out of 5 average rating, 609 reviews

Buffalo Springs Distilling Company

On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week

22–29 Mar

$292 NZD per night

Guest favourite

Home in Bedford

4.99 out of 5 average rating, 188 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

28 Jul – 4 Aug

$278 NZD per night

Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 35 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

22–29 Aug

$237 NZD per night

Guest favourite

Barn in Mount Eden

4.98 out of 5 average rating, 121 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

4–11 Sep

$231 NZD per night

Guest favourite

Tiny home in La Grange

4.98 out of 5 average rating, 161 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

8–15 Dec

$189 NZD per night

Guest favourite

Home in Pleasureville

5.0 out of 5 average rating, 82 reviews

Pleasureville - The name says it ALL

This location is a Pleasure! Cozy Kentucky home off the beaten path, but close to attractions. Imagine after a full day on the bourbon trail enjoying your own piece of Kentucky with a drink in your hand. Access to 25+ acres of beautiful farmland and super clean, fully stocked private home. Close to the Outlet Shoppes of the Bluegrass making it a perfect ladies weekend get away. Additional meeting/event space available in the renovated on site barn. Reminder No Pets allowed.

30 Mar – 6 Apr

$256 NZD per night

Guest favourite

Bungalow in Dry Ridge

4.97 out of 5 average rating, 576 reviews

The Cute Little House Near The Ark Encounter

The "Little House" is a cute 1 bedroom house located on our farm in a beautiful country setting with 6 acres of outdoor space for relaxing. It is separate from our home and is all yours. It is conveniently located only 8 miles from the Ark Encounter and you only need to make one turn to get there. We have chickens, ducks, rabbits, a horse, and 2 goats. We also have a 1/2 mile nature trail to explore with a scavenger hunt, and a campfire spot with free firewood.

24–31 Oct

$202 NZD per night

Guest favourite

Condo in Shelbyville

4.94 out of 5 average rating, 124 reviews

Horses, Bourbon, and More .... Shelbyville Condo

Beautiful condo duplex features 2 bedrooms / 2 full bathrooms, light open floor plan, private entrance with parking at the door.. Close to shopping, expressway, local wineries, bourbon distilleries, horse farms and much more!! Fully Furnished including linens, towels, dishes and more! Work or travel, we welcome you to your home away from home! Located Close to shopping, farms, local interests and I64.. 25 minutes to Louisville, 45 minutes to Lexington.

5–12 Aug

$226 NZD per night

Guest favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 449 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

22–29 Jan

$211 NZD per night

Guest favourite

Tiny home in Frankfort

4.98 out of 5 average rating, 335 reviews

Tiny Home with Huge Charm near the Elkhorn Creek

Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!

30 Jul – 6 Aug

$194 NZD per night

Guest favourite

Cottage in Pleasureville

4.99 out of 5 average rating, 174 reviews

The Cozy Cottage on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery, it is also in close proximity to a gas station, grocery and library. Located in the heart of an Amish community, you will hear horses and buggies clip-clopping past as you sip your morning coffee. This cottage is on a functioning farm with horses, cats, goats and donkeys, with overnight housing facilities for your own equines as well.

23–30 Jul

$209 NZD per night