Vacation rentals with a hot tub in Shelby County

An outdoor fire pit area is featured, surrounded by several adirondack chairs arranged on a gravel surface. String lights illuminate the space, creating a warm ambiance. In the background, the house is partially visible, with an inviting seating area under a canopy.

4.98 out of 5 average rating, 64 reviews

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Gather your crew for an unforgettable stay in Kentucky bourbon country. Magnolia Bourbon Manor is a beautifully restored historic home that sleeps 10, featuring a private speakeasy, covered hot tub, fire pit, and pool-table game room. Just 3 minutes from downtown Shelbyville, 12 minutes from Jeptha Creed and Bulleit, and 35 minutes from Louisville, it’s the perfect home base for Bourbon Trail adventures, weekends with friends, family getaways, and celebrations. Proudly hosted by a Superhost and

BathroomHot tubComfort

4.95 out of 5 average rating, 74 reviews

A spacious living area is furnished with a mix of comfortable sofas and armchairs in neutral tones. A modern coffee table is centered on a plush area rug. A large television is mounted on the wall, and natural light is allowed to enter through two windows.

Home in Frankfort

Close to Buffalo Trace •Hot Tub• Grill • Nature

Bourbon Hills Retreat is a newly renovated 4BR, 2.5BA farmhouse on 13 private acres with stunning hilltop views. View the hollers of KY while watching the deer cross the yard. Sleeps 8 comfortably. Enjoy the hot tub, porch rocking chairs, starry nights, and peaceful surroundings. Minutes from Buffalo Trace & Bulleit, horse tracks, wineries, and Bourbon Trail favorites. Centrally located between Louisville & Lexington—perfect for family getaways, couples, or group trips exploring Kentucky’s best!

BathroomOutdoor spacesLocation

5.0 out of 5 average rating, 21 reviews

Home in Waddy

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.

Outdoor spacesHot tubLocation

4.97 out of 5 average rating, 29 reviews

Home in Waddy

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

Cat Ridge Resort is a modern, professionally designed private retreat in the heart of Kentucky bourbon country, perfect for unforgettable group getaways. Explore iconic distilleries by day, then return to luxury amenities and warm Southern hospitality—from a private speakeasy and relaxing wellness spaces to games, a firepit, outdoor lounges, chipping green, and more. 🥃 5 top distilleries within 25 minutes ✈️ Conveniently located between LEX & SDF 📍 Shelbyville & Lawrenceburg w/in 25 minutes

Hot tubOutdoor spacesAccess

4.96 out of 5 average rating, 92 reviews

The covered porch is adorned with sheer white curtains and warm string lighting, creating a cozy atmosphere. Plush seating and a decorative rug invite relaxation. A hot tub and additional seating are visible, enhancing the outdoor living space's comfort and charm.

Cottage in Shelbyville

Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby

Soak in your private hot tub, step into a one-of-a-kind art gallery, and wake up 30 minutes from the Kentucky Derby. This renovated Victorian cottage blends spa-level comfort with local artistry, the perfect base for Bourbon Trail adventures, horse show weekends, or a group getaway nobody will forget. Three ensuite bedrooms, a gourmet kitchen, and a covered porch await. ✔ Hot Tub · Art Gallery ✔ 3BR/3BA Ensuite · Bourbon Trail ✔ KY Derby 30 min · BBQ Porch ✔ Wi-Fi · Smart TVs · Self Check-In

Outdoor spacesBathroomLocation

4.94 out of 5 average rating, 112 reviews

A circular fire pit area is surrounded by six blue Adirondack chairs, positioned on a green lawn. The cabin, featuring a green metal roof and wooden exterior, is visible in the background among tall trees and open space.

Cabin in Shelbyville

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.

Outdoor spacesHot tubCleanliness

4.83 out of 5 average rating, 36 reviews

Home in Bagdad

*NEW* hot tub-sauna-large pool-game room-speakeasy

Escape to comfort and style at Expression on the Rocks: A newly renovated 6BR, 4400 sq ft retreat in the heart of the Bourbon Trail. Set on 5 lush acres with scenic views of hills and wildlife, this home offers a hot tub, sauna, inground pool, firepit, speakeasy w/poker lounge, and gameroom. Perfect for group getaways-just minutes from Kentucky’s world-famous distilleries. Who needs to be the center of the universe when you can stay in the center of the Bourbon Trail? Book Now!

BathroomHot tubLayout

4.93 out of 5 average rating, 73 reviews

Peaceful Bourbon trail home POOL hot tub 3 kings

This quiet Bourbon Trail home is designed for groups, with three king beds, one queen, and a twin daybed. The hot tub, pool table, and fully-stocked kitchen make group meals and relaxation easy. Open living and dining areas provide space to gather. Outside, a large dining area and separate seating area let you unwind. Grocery stores, restaurants, and distilleries are all nearby. The pool is open May - September, and the property is maintained for comfort and reliability.

Outdoor spacesBathroomAccess

5.0 out of 5 average rating, 32 reviews

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.

Outdoor spacesBathroomIndoor spaces

An aerial view showcases a spacious estate with bright outdoor lighting highlighting the landscaped grounds. A recreational area featuring basketball courts and seating is visible, offering ample space for outdoor activities, while the elegant façade of the home provides an inviting presence.

4.99 out of 5 average rating, 68 reviews

Kentucky Estate: Speakeasy, Theater & Sleeps 20

Oak & Ember Estate is an 8-bedroom Kentucky retreat sleeping up to 20 on 5 private acres. Hidden speakeasy with poker table, private cinema, converted garage game room with putting green and billiards, hot tub, pickleball court, and a gourmet kitchen built for groups. 30 minutes from Churchill Downs. The perfect home base for bourbon trail adventures, Derby weekend, family reunions, and corporate retreats. Guests say they never wanted to leave.

Hot tubBathroomIndoor spaces

4.98 out of 5 average rating, 161 reviews

The modern farmhouse is viewed from an elevated angle, showcasing a large backyard with a well-maintained lawn. Multiple windows reflect the soft colors of sunset. A covered patio area is visible, complete with seating. Games such as corn hole are set up on the grassy area.

Home in Bagdad

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!

Outdoor spacesHot tubSleep quality