Holiday rentals with a patio in Shelby County

5 out of 5 average rating, 105 reviews

A log cabin is set against a vibrant sunset, highlighting its wooden exterior and spacious porch. Lush green grass surrounds the cabin, complemented by flower beds and gravel pathways. The rear showcases windows and entrance doors that invite natural light into the home.

Cabin in Frankfort

Bourbon Trail Cabin~Enjoy Christmas decor in Dec!

🌲FOR CHRISTMAS- home is transformed into cozy holiday cabin retreat! 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 plenty of fun 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!

4.97 out of 5 average rating, 159 reviews

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Guest suite in Shelbyville

A spacious living area is showcased with a large sectional couch in brown leather, complemented by decorative cushions. A round, patterned coffee table sits in front, while soft light filters through the window blinds, providing a cozy ambiance. Wall artwork adds character to the room.

4.95 out of 5 average rating, 22 reviews

Country guest suite. Bourbon trail close by.

Welcome to Kentucky! We have the perfect newly renovated guest suite for visitors whether you are headed to our famous Kentucky Derby, Bourbon Trail tours, or more. You will have your private entrance, a comfortable living area, a fully stocked kitchenette, a full bath, one bedroom with a queen bed, and a living room with a large sectional couch and TV. WiFi is available, and we are a short drive to Frankfort, Louisville, and Bardstown. #distillerytours#bourbon #bourbontrail #derby#railfest

5 out of 5 average rating, 44 reviews

A hot tub is situated under an awning, surrounded by soft, white curtains that provide privacy. The bubbling water reflects the greenery of trees beyond, enhancing the serene atmosphere of the outdoor area.

Cottage in Simpsonville

The Miles Around Kentucky Cottage| Hot Tub

Welcome to The Miles Around Kentucky Cottage! Relax and rejuvenate in our cozy cottage nestled in a private area yet still close to stores, restaurants and many tourist attractions including 1.5 miles to the Bluegrass Outlet Mall. Only one mile from small town businesses including Little Mount Lavender, Brick and Mortar Coffee, Weathered Oak, The Lovely Fig, Dos Mundos and El Nopal. 25 miles to Buffalo Trace and downtown Louisville attractions. Centrally located to Louisville & Lexington.

A charming 1920s stucco home is displayed against a clear blue sky. The exterior features a dark metal roof and large windows, surrounded by a well-maintained lawn and landscaping. Trees in the background indicate the rural setting of the property.

4.92 out of 5 average rating, 13 reviews

Hillside view/ bourbon trail fun game room

Welcome to Oakdale! Located just minutes from the interstate on a 95 acre farm in Shelby County. This cute 1920’s stucco home was recently renovated so your family could enjoy the beautiful views on the countryside. Each room is decorated to keep the older southern charm. Oakdale offers 3 bedrooms, 2 full baths, game room and custom bunk beds! Around 30 miles to Churchill downs or Keeneland. Less than 10 miles from Jeptha Creed and Bulliet Distillery. Around 15 miles to taylorsville lake

4.96 out of 5 average rating, 53 reviews

A modern staircase with a black railing leads to the upper level, illuminated by a geometric chandelier. A small wooden desk, adorned with flowers, sits against the wall, alongside a decorative sign reading 'Maple's Place.' Natural light streams in through a skylight above.

Farm stay in Crestwood

Maple's Place - *charm*country*hot tub*bourbontour

Maples Place Built in 1890 and meticulously remodeled down to the studs, Maple's Place combines historic charm with modern amenities. The house has all-new HVAC, electrical, plumbing, roofing, and siding. The home features three beautifully decorated bedrooms, two full bathrooms, and one half-bath. The master bath is a haven of luxury with a walk-in shower and a soaking tub. Each room is thoughtfully designed. Outside, enjoy a spacious deck and pergola, complete with an 8-person hot tub.

Guest suite in Shelbyville

A vibrant sunset casts pink and orange hues across the sky, framed by trees in the foreground. A grassy lawn extends into the background, with a rustic shed visible among the trees, offering a serene countryside view.

4.98 out of 5 average rating, 66 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

A panoramic view reveals lush greenery along Guist Creek Lake, with gentle contours of the landscape reflected in the water. The image captures a spacious deck equipped with seating, creating a serene spot for relaxation and observation of the natural beauty.

4.95 out of 5 average rating, 37 reviews

Bourbon by the Lake

Peaceful, Beautiful 4 bedroom, 2 bathroom house sitting on Guist Creek Lake in Shelbyville, KY located very close to the Bulleit Bourbon Distillery. Lake view from two of the four bedrooms. Perfect for bird watching. Guist Creek Lake is a great kayaking and fishing lake. Patio off the main living room with patio table and chairs. Two comfortable living room spaces with smart TVs, games, and books. Beautiful sunroom overlooking the lake. Nice patio space. Lake access with boat dock.

The spacious living room features large circular windows that provide ample natural light. Two comfortable sofas, one in a warm rust color and another in dark upholstery, are arranged around a decorative coffee table. An elegant area rug enhances the warmth, while indoor plants add a touch of greenery.

4.96 out of 5 average rating, 70 reviews

Cozy Kentucky Winter, Bourbon Trail, Location!

♡ Meet The Blue Belle: a beautifully restored 1880s cottage ON the Bourbon Trail, nestled on a peaceful block in the heart of Shelbyville. Start your day with a coffee on the back deck, make s'mores by the fire pit, cook dinner in the fully stocked kitchen, & cozy up in the living room for movie night after a long day of exploring & bourbon! A short drive to Louisville, Lexington, & Frankfort and other great areas. Comfortably sleeps 8. Perfect for families & couples!

5 out of 5 average rating, 19 reviews

A two-story guest house is situated amid lush green grass and shade trees. The exterior features a combination of light siding and dark accents, with a covered porch furnished with chairs. Windows allow natural light to engage the interior, enhancing the peaceful rural setting.

Farm stay in Shelbyville

Annola Farm Guest House

Stay and be delighted with this newly renovated two-story guest house which adjoins our 11-stall horse barn. Framed by covered porches and shade trees, our guest house is a wonderful place to unwind and relax during your stay in beautiful central Kentucky. The best of both worlds--a lovely rural setting situated only minutes from the interstate, making travel to Churchill Downs, Valhalla Golf Course, and other attractions in nearby Louisville and Frankfort a breeze.

A modern rural structure is showcased with a spacious wooden deck that extends across the front. String lights are suspended above, adding a soft glow. The surrounding landscape features a grassy area and a black wooden fence, with trees in the background.

4.98 out of 5 average rating, 47 reviews

The Back 40 ~ Modern*Scenic*Private*EV Charger

The Back 40...where rural charm meets the modern amenities you expect. Overlooking the Jeptha Creek and situated in a serene Kentucky cattle pasture, this piece of country gold is your gateway to Kentucky's lauded Bourbon Trail and the Saddlebred Capital of the World. The Back 40 is perfect for Bourbon Trail adventurers, those seeking a little retail therapy, or folks simply aiming to escape to a slower pace of life for just a spell.