Pleasureville Vacation Rentals from CA $150: Short-Term Rentals for 2026

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Our top choices for Pleasureville vacation rentals

A bar area with stools, a counter, and a television mounted on the wall.

1. Unique Downtown Studio with an Industrial Vibe

Shelbyville

Kathleen S.

CA $315 total

includes taxes & fees

Nov 3 - Nov 4

A two-story building with a dark facade, a red door, and a sign that reads 'The Stables.'

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

Shelbyville

Kim K.

CA $258 total

includes taxes & fees

Nov 15 - Nov 16

A modern cabin with a wooden deck and a balcony, surrounded by a natural landscape.

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

Frankfort

Terry-Ann

CA $351 total

includes taxes & fees

Oct 25 - Oct 26

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

4. Kentucky Bourbon Trail: Hot Tub & Game Room

Bagdad

Hannah G.

CA $847 total

includes taxes & fees

Nov 2 - Nov 3

A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

5. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Frankfort

Teresa M.

CA $232 total

includes taxes & fees

Oct 25 - Oct 26

A living room with a sofa, a coffee table, a rug, and a bookshelf.

6. Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Frankfort

Darby D.

CA $232 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

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

Waddy

Daniel H.

CA $393 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a porch, a small garden, and a sign that reads "Hotel."

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

Shelbyville

Donald A.

CA $421 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

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

Waddy

Anthony T.

CA $447 total

includes taxes & fees

Oct 28 - Oct 29

A bathroom with a white sink, a mirror, and a shower curtain.

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

Frankfort

Jacinda C.

CA $356 total

includes taxes & fees

Oct 26 - Oct 27

A log cabin with a fire pit and outdoor seating.

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

Frankfort

Michael I.

CA $631 total

includes taxes & fees

Nov 8 - Nov 9

A reception area with a mounted TV displaying various streaming services, a wooden console with a welcome sign, and a seating area with a table and chairs.

12. Capital City Condo #10

Frankfort

Amanda L.

CA $232 total

includes taxes & fees

Oct 25 - Oct 26

A beige sofa with patterned cushions, a dark patterned rug, and a window with blinds.

13. Capital City Condo #8

Frankfort

Robert V.

CA $232 total

includes taxes & fees

Nov 1 - Nov 2

A modern cabin with a wooden deck, a covered outdoor seating area, and a bright orange door.

14. Scenic Highgrounds Modern Cabin - Chicory

Frankfort

Rob L.

CA $423 total

includes taxes & fees

Oct 25 - Oct 26

A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

15. Beautiful restored Victorian farmhouse

Shelbyville

Joann E.

CA $627 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

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

Frankfort

Sabrina P.

CA $689 total

includes taxes & fees

Nov 8 - Nov 9

A log cabin with a covered porch, large windows, and a well-maintained front yard.

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

Shelbyville

Bobby E.

CA $807 total

includes taxes & fees

Oct 22 - Oct 23

A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

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

Bagdad

"We had a fantastic holiday weekend at this property - Two families (4 adults, 4 kids) stayed with plenty of room and amenities. This house could have easily slept more. Communication from the host was clear and prompt. The kids absolutely loved the game room and adults enjoyed the ample living spaces on both the main floor and the basement. Although we didn't use the pool given the time of year, the hot tub, sauna, and fire pit were great! Our kids loved seeing the horses all around...

Justin C.

CA $1,299 total

includes taxes & fees

Oct 22 - Oct 23

A wooden sign with "Capital City Cottage" written on it, placed in front of a white picket fence.

19. Capital City Cottage

Frankfort

Tim W.

CA $351 total

includes taxes & fees

Nov 2 - Nov 3

A cozy room with a large window, a wooden table with a blanket and a notebook, and a red pillow.

20. Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail

Owenton

Mary S.

CA $169 total

includes taxes & fees

Nov 1 - Nov 2

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Top Pleasureville Hotel Reviews

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent

"The motel is under a little construction. But our stay was great. It is at a peaceful location. We saw deer out the window different times. The breakfast was very good and there was always plenty of it. We will be staying there if we are that way in our travels again."

The North Star Inn

8/10 Good

"The property is being updated. The owner met us at the property. The room was clean and comfortable. Small, but full-sized refrigerator, microwave and toaster. Close to a family-run restaurant/truck stop. Close to route 71. AC/and heat. We needed both during our stay. Shower/tub has slip resistant bottom."

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 $150 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.

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Check prices for these dates

Our top choices for Pleasureville vacation rentals

1. Unique Downtown Studio with an Industrial Vibe

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

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

4. Kentucky Bourbon Trail: Hot Tub & Game Room

5. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

6. Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

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

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

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

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