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    Check prices for these dates

    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Pleasureville holiday homes

    1. Haven of the Bluegrass | Bourbon Trail Getaway!

    A fire pit with chairs around it in a grassy outdoor area.

    2. The Shelby House | Historic Charm, Modern Comfort

    A porch with two wooden chairs and a table, white siding, and a window.

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

    A living room with a large TV mounted on the wall displaying a race track, a wooden cabinet with glass doors, a dining area with a table and chairs, and a small side table with a radio.

    4. Kentucky Bourbon Trail: Hot Tub & Game Room

    An outdoor patio with wicker furniture, a central fire pit, and string lights.

    5. Quiet Downtown Maple Cottage Gem

    A modern kitchen with black cabinets, a central island, and wooden shelves above a textured backsplash.

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

    A white building with a porch and four white Adirondack chairs facing a grassy field.

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

    A modern kitchen with white cabinets, a marble floor, a farmhouse-style accent wall, and a kitchen island with a towel rack.

    8. Bourbon Trail | 4BR, Sleeps 10, Barrel Sauna, Hot Tub, Gym, Game Room, Fire Pits

    A kitchen with a coffee maker, a water dispenser, and a bottle holder with three bottles.

    9. This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

    A wooden deck with a view of a cityscape, a wooden bench, and a table with chairs.

    10. Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views

    A modern kitchen with a central island, stainless steel appliances, and a blue accent wall.

    11. University Stay | Sleeps 10 | Game Room + Firepit + Grill

    A living room with a brick wall, a ceiling fan, a sofa, an orange chair, and a painting.

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

    A wooden shelf with framed artwork, a thank you box, and a remote control.

    13. Spacious Bourbon retreat near Downtown Louisville!

    A covered deck with a railing, a white building with large windows, and a metal roof.

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

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

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

    A porch with white rocking chairs and a wooden floor.

    16. the bourbon barrel escape HotTub Game Room pets ok

    A hot tub with a wooden deck and outdoor furniture.

    17. Miss Reba's Love is a charming house with a warm Kentucky feel.

    A kitchen with a wooden countertop, a white vase with dried flowers, and a gold decorative sign on the wall.

    18. Bourbon Trail Lakehouse

    A covered deck with outdoor furniture, a grill, and a view of a lake and surrounding houses.

    19. This gem sits in the heart of picturesque South Frankfort, near the Kentucky river

    A spacious living room with a fireplace, leather furniture, and a large TV mounted on the wall.

    20. Bourbon trail - conveniently located 8 min to buffalo trace

    Private kitchen

    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 reviews in Pleasureville

    Candlewood Suites Shelbyville by IHG

    An outdoor patio area with wicker furniture and a pergola.

    Hampton Inn Simpsonville

    A Hampton Inn hotel with a modern design, featuring a prominent entrance and a well-lit parking area.

    The Delegate

    A bar area with a counter, stools, and a hanging light fixture.

    Best Western Shelbyville Lodge

    A spacious living area with leather sofas, a fireplace, and a view of the outdoors.

    Fairfield Inn & Suites by Marriott Frankfort

    A hotel lobby with a reception desk, a dining area, and seating with a blue patterned carpet.