Vacation rentals in Pleasureville

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Top-rated vacation rentals in Pleasureville

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Guest favorite

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!

Sep 2 – 9

G$34,649 GYD per night

Guest favorite

Farm stay in Williamstown

4.99 out of 5 average rating, 376 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.

Dec 6 – 13

G$26,677 GYD per night

Guest favorite

Home in Stamping Ground

4.97 out of 5 average rating, 604 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

Mar 3 – 10

G$32,888 GYD per night

Guest favorite

Cabin in Sadieville

4.97 out of 5 average rating, 247 reviews

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

Jul 29 – Aug 5

G$21,057 GYD per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 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

Dec 7 – 14

G$20,441 GYD per night

Guest favorite

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.

Jan 29 – Feb 5

G$29,208 GYD per night

Guest favorite

Condo in Shelbyville

4.89 out of 5 average rating, 109 reviews

Your Kentucky Home Away From Home

Lovely, renovated Patio Home features 2 bedrooms and 2 full baths – one with a low-entrance shower and one with a full tub. This Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, washer and dryer, wall-mounted flat-screen television, tasteful art, linens, towels and more. This is your home away from home!

Oct 5 – 12

G$24,394 GYD per night

Guest favorite

Cabin in Madison

4.98 out of 5 average rating, 384 reviews

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

Apr 1 – 8

G$33,612 GYD per night

Guest favorite

Farm stay in Shelbyville

5.0 out of 5 average rating, 16 reviews

Bourbon trail apartment on horse farm

Don't just visit Kentucky, experience it! Join us at Celebration Acres in beautiful Shelbyville. Centrally located between Louisville & Lexington, this private unit is your refuge as you explore bourbon country. We're 5 min from Bulleit, & under 20 miles to Jeptha Creed & Buffalo Trace. Here for the horses? We're close to Kentucky Horse Park & Churchill Downs. Our horses & donkeys are on property & available for a meet & greet for a unique memory & photo opportunity.

Dec 28 – Jan 4

G$20,365 GYD per night

Guest favorite

Bungalow in Dry Ridge

4.97 out of 5 average rating, 569 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.

Sep 24 – 29

G$23,547 GYD per night

Guest favorite

Tiny home in Frankfort

4.98 out of 5 average rating, 331 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!

Aug 17 – 24

G$21,778 GYD per night

Guest favorite

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.

Jul 3 – 10

G$25,473 GYD per night