Pleasureville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Pleasureville vacation rentals

A covered outdoor patio with wicker furniture, a fire pit, and string lights.

1. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
The price is CA $231
CA $787 total
includes taxes & fees
Nov 9 - Nov 10
Kentucky Bourbon Trail: Hot Tub & Game Room
A log cabin with a covered porch, large windows, and a well-maintained front yard.

2. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Shelbyville
10.0 out of 10, Exceptional, (12 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is CA $680
CA $823 total
includes taxes & fees
Nov 9 - Nov 10
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

3. *NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Bagdad
9.6 out of 10, Exceptional, (10 reviews)
"My family & I had a great time at the house. My grandkids loved the pool. It was a very enjoyable stay."
United States
LORI T.
The price is CA $470
CA $1,237 total
includes taxes & fees
Nov 9 - Nov 10
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A log cabin with a porch, a door with a window, and a swing.

4. Sip on bourbon in the hot tub! +hiking & game shed

Sip on bourbon in the hot tub! +hiking & game shed
Frankfort
9.4 out of 10, Exceptional, (6 reviews)
"Family friendly"
United States
Michael I.
The price is CA $320
CA $583 total
includes taxes & fees
Nov 17 - Nov 18
Sip on bourbon in the hot tub! +hiking & game shed
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

5. Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful and spacious! The host has thought of absolutely everything. We had a wonderfully relaxing time and the beds are SUPER comfortable! It's a perfect blend of being "out in the country" and close enough to civilization that you don't feel isolated."
United States
Sabrina P.
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

6. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (16 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is CA $312
CA $598 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful restored Victorian farmhouse
A kitchen with a gas stove, a coffee maker, and built-in ovens.

7. Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (22 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is CA $134
CA $246 total
includes taxes & fees
Dec 1 - Dec 2
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A modern cabin with a wooden deck and a balcony, surrounded by a natural landscape.

8. Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Frankfort
9.6 out of 10, Exceptional, (26 reviews)
"What a great cabin it was so clean and cute and had everything that we needed a great place to stay"
United States
Jessica S.
The price is CA $198
CA $338 total
includes taxes & fees
Nov 12 - Nov 13
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Two cabins with wooden decks and black exteriors, set in a forested area with a clear sky.

9. Two Bourbon Barrel Cabins

Two Bourbon Barrel Cabins
Frankfort
9.8 out of 10, Exceptional, (29 reviews)
"The cabins worked perfectly for our group! Close to town and distilleries we visited."
United States
shannon J.
The price is CA $396
CA $619 total
includes taxes & fees
Nov 12 - Nov 13
Two Bourbon Barrel Cabins
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

10. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is CA $208
CA $396 total
includes taxes & fees
Nov 15 - Nov 16
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A room with a leather sofa, two armchairs, a bed, and a small table with a tray.

11. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is CA $127
CA $238 total
includes taxes & fees
Nov 9 - Nov 10
Unique Downtown Studio with an Industrial Vibe
A two-story house with a front porch, columns, and a well-maintained lawn.

12. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Shelbyville
10.0 out of 10, Exceptional, (25 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is CA $747
CA $902 total
includes taxes & fees
Nov 15 - Nov 16
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

13. Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
Waddy
10.0 out of 10, Exceptional, (2 reviews)
"The place was great. Tucked away off the main highway and between bourbon country’s best. Well stocked amenities and little things provided that were a great touch. Will be back again!"
United States
Daniel H.
The price is CA $168
CA $374 total
includes taxes & fees
Nov 9 - Nov 10
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

14. Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
La Grange
10.0 out of 10, Exceptional, (10 reviews)
"Very nice house, spacious, clean and very comfortable. Perfect for our stay to attend a conference in the area. Highly recommend!!"
United States
Jessica B.
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

15. Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
9.0 out of 10, Wonderful, (12 reviews)
"Excellent stay and a beautiful property. Perfect for our needs no complaints."
United States
Anthony T.
The price is CA $98
CA $575 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A kitchen with a central island, wooden ceiling, and bar stools.

16. On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace

On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
Waddy
9.0 out of 10, Wonderful, (7 reviews)
"Some friends and I were in town for a bourbon tour and a Keeneland visit. The property is gorgeous, and centrally located between Lexington and Louisville, The house is immaculate and perfect for a trip like this. The host is excellent, and every detail of the property was thought of. Our stay was over and above anything we imagined. Thank You!! "
United States
Timothy S.
The price is CA $357
CA $1,090 total
includes taxes & fees
Nov 10 - Nov 11
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
A spacious living room with two grey sofas, a wooden bookshelf, and a staircase leading to an upper level.

17. H-DERBY, Keeneland, Bourbon or Family Gathering!

H-DERBY, Keeneland, Bourbon or Family Gathering!
Frankfort
9.8 out of 10, Exceptional, (88 reviews)
"Another great trip to the Bourbon Trail with the guys. Great house in a perfect location."
United States
Jason M.
The price is CA $572
CA $963 total
includes taxes & fees
Nov 9 - Nov 10
H-DERBY, Keeneland, Bourbon or Family Gathering!
A modern living room with a sofa, a coffee table, and a bed.

18. The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
9.8 out of 10, Exceptional, (40 reviews)
"Great property and wonderful hosts! "
United States
Jacinda C.
The price is CA $140
CA $327 total
includes taxes & fees
Dec 7 - Dec 8
The Bourbon Garage- walking distance to Buffalo Trace!
A cozy cabin interior with a stone fireplace, a leather sofa, and a large window offering a view of the outdoors.

19. Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
Shelbyville
10.0 out of 10, Exceptional, (13 reviews)
"Nice stay"
United States
Jackie S.
The price is CA $1,404
CA $2,337 total
includes taxes & fees
Dec 7 - Dec 8
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
A wooden deck with a green door, wicker chairs, and a small table.

20. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (7 reviews)
"I loved having the travel crib and high chair available for my kids! Everything was clean and the host made everything a breeze!"
United States
Samantha C.
The price is CA $380
CA $625 total
includes taxes & fees
Nov 15 - Nov 16
The Sweet Retreat Wheelchair Accessible Historic Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasureville Hotel Reviews

A lobby with a wooden ceiling, a beige sofa, two armchairs, a patterned rug, and a reception desk.
Holiday Inn Express & Suites La Grange by IHG

Holiday Inn Express & Suites La Grange by IHG

Holiday Inn Express & Suites La Grange by IHG
La Grange

10/10 Excellent

Nice and clean will stay again.
Canada
Sharlene
Reviewed June 10, 2023
Holiday Inn Express & Suites La Grange by IHG

Find out more about Pleasureville

Everything you need to know about Pleasureville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasureville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasureville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasureville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasureville. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasureville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasureville vacation rentals we have selected for you start as low as CA $84 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pleasureville rentals

At Expedia, we put the best Pleasureville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasureville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasureville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasureville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Pleasureville?

Yes, we have vacation rentals close to the most popular sights in Pleasureville, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Pleasureville has to offer?

Charming 2-bedroom house on our farm with beautiful sunsets: This vacation home rental near Pleasureville is located in a rural location and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Pleasureville?

Explore the area and family-friendly sights such as La Grange Railroad Museum & Learning Center, or get out into nature at a spot like Ohio River Valley. In the larger area, you’ll find Bulleit Distilling Co. and Jeptha Creed Distillery.

What are vacation rentals like in Pleasureville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Pleasureville. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.