Holiday rentals with a hot tub in Shelby County

Bourbon Trail Estate | Theater, Games & Hot Tub

✨ Escape to The Bourbon Barrel Retreat ✨ Designed for bourbon trail weekends, family gatherings, and group getaways, this modern 6-bedroom retreat sleeps 16 and is built for making memories. Relax in the hot tub after the distilleries, challenge friends in the game room, enjoy movie nights in the private theater, or gather around the firepit. Next door is a cozy farm with horses! Located just minutes from Kentucky's most popular distilleries. 🌟 BOOK YOUR STAY TODAY! 🌟 Please note: No weddings.

The Rec Farm-Log Cabin, Private Lake & Arcade

Previously one of Shelbyville’s favorite with 4.95 rating and 80+ reviews — now refreshed under new ownership, same great experience! The Rec Farm—a private 13 acre pet friendly retreat with a renovated log cabin, serene lake views, hot tub, campsite and game-packed Rec Barn featuring ping pong, ski ball, and more. This hidden retreat combines rustic charm and modern comfort just minutes from I-64. Perfect for families, friends, and bourbon explorers looking to relax, reconnect, and unwind.

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

Red Bridge Retreat

Red Bridge Retreat is your perfect Christmas getaway! Set on 5 serene acres just outside Louisville, you’re only 30 minutes from major holiday events. Elegant, stylish décor throughout. This 4-bed, 3-bath private home features a kitchen deck with a Blackstone & gas grill, a covered patio with HOT TUB, a covered fire-pit area, a fully equipped kitchen, a game room with bumper pool & Pac-Man, and a tree-lined drive. It even includes a bourbon-themed lounge to unwind and relax.

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

6 Private Acres! HotTub/Theater | Gamerm | Arcade

Minutes from Kentucky's most iconic distilleries, Oak & Mash is a private six-acre log cabin retreat designed for unforgettable group getaways. Relax in the covered hot tub, enjoy movie nights in the home theater, gather in the bourbon lounge, challenge friends to pool, shuffleboard, or arcade games, and unwind around the fire pit beneath the stars. With indoor and outdoor entertainment for every season, there's something for everyone to enjoy.

Bourbon Trail Retreat: Pool, Hot tub & Game Room

Welcome to The Shelby Stop where comfort & style awaits you! This 4 bedroom, 2.5 bath home offers space for everyone. 2 bedrooms are on the main floor; 1 of which is the luxury primary bedroom with en-suite bathroom. 1/2 bathroom just off the kitchen. The primary bedroom is a beautiful room with king size bed, luxury mattress, linens, large smart TV, sitting chair, & full size mirror. The attached en-suite bathroom is newly renovated in 2023

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!

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

A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

Private A-frame Cabin | Hot tub, Firepit & Views

Welcome to Peletah Escape — our family’s cherished retreat nestled in Kentucky’s rolling hills. This cozy cabin offers sweeping views, a wraparound porch, hot tub, fire pit, game room, and plenty of space to relax. Inside, you’ll find rustic charm with modern comforts, from a fully stocked kitchen to comfy beds and a bourbon bar. Whether you're here to unwind or explore, Peletah Escape is your perfect Bluegrass getaway.

Hot Tub | Firepit | Putting Green | 5 Bedrooms

Picture this: the fire pit crackles while bourbon stories spill into the Kentucky night, steam rises off the hot tub under string lights, and someone's lining up a putt on your own backyard green. Ten of your favorite people, one quiet Shelbyville street, minutes from the world's most famous bourbon trail. This isn't just somewhere to sleep between distillery tours — it's the trip everyone keeps talking about after.

1909 BourbonTrail Gem | 4 King Beds | Fire Pit

Discover The Copper & Oak, a beautifully restored 1909 home in downtown Shelbyville. This spacious 4-bedroom, 4-bath property features two full living spaces connected by a speakeasy-style door, fully stocked kitchens, king bedrooms, and cozy gathering areas. Enjoy shuffleboard, the covered patio, and walkable access to shops, dining, and the Kentucky Bourbon Trail. Perfect for groups seeking comfort and charm.