Vacation rentals with outdoor seating in Shelbyville

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Top-rated accommodations with outdoor seating in Shelbyville

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Top guest favourite
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
5 out of 5 average rating, 107 reviews

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!

Top guest favourite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg
4.99 out of 5 average rating, 455 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top guest favourite
Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.
Guesthouse in Nicholasville
4.98 out of 5 average rating, 365 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Guest favourite
A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.
Cabin in Louisville
4.95 out of 5 average rating, 349 reviews

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Top guest favourite
The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.
Cabin in Louisville
4.99 out of 5 average rating, 243 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favourite
A well-equipped kitchen features a spacious wood island with two upholstered stools. Modern appliances, including a gas range and sleek cabinetry, complement the space. Natural light streams through the windows, enhancing the inviting atmosphere, while tasteful decor adds a touch of character.
Loft in Frankfort
4.98 out of 5 average rating, 194 reviews

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and charm of The Loft your top-rated fall retreat just 8 minutes from downtown. Stroll to the Capitol, see the autumn sights, and take in Horse Country nearby. Snuggle into a cozy bed, curl up on the couch, and enjoy modern touches in your private second-floor hideaway. With parking at the door and a hygge-inspired vibe, it’s perfect for crisp days and cozy nights. Just minutes from 13 distilleries, The Loft is your ideal base for a stylish Bourbon Trail escape.

Top guest favourite
A spacious studio-style room features a four-poster bed with white bedding. A comfortable armchair sits nearby, and a flat-screen TV is positioned on a wooden entertainment unit. Natural light enters through patterned curtains, illuminating the warm wood flooring.
Tiny homes in La Grange
4.98 out of 5 average rating, 238 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Top guest favourite
A cozy living area showcases a black loveseat paired with a distinctive armchair, positioned on a patterned cowhide rug. Natural light enters through a large arched window, illuminating the wooden accent wall and framed artwork of a horse.
Cottage in Pleasureville
4.99 out of 5 average rating, 222 reviews

Tiny House Farm Stay on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery. Located in the heart of an Amish community. We breed, show and raise registered myotonic goats. We have a fall and spring kidding season so if you book during that time, expect to see baby goats frolicking in the fields. The cottage is on a functioning farm with horses, cats, goats and a donkey. We offer overnight housing facilities for your own equines as well.

Top guest favourite
A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.
Guesthouse in Shelbyville
4.98 out of 5 average rating, 122 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Top guest favourite
A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.
Guesthouse in Frankfort
4.99 out of 5 average rating, 130 reviews

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Top guest favourite
A gravel path leads up to the cabin, surrounded by lush greenery and tall trees. The cabin's exterior features a mix of wood and metal siding, with a deck extending from the entrance, providing a connection to the natural surroundings.
Cabin in Lawrenceburg
4.99 out of 5 average rating, 100 reviews

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

Top guest favourite
The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.
Guest suite in Louisville
4.99 out of 5 average rating, 210 reviews

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Popular amenities for Shelbyville outdoor seating rentals

Quick stats about vacation rentals with outdoor seating in Shelbyville

  • Total vacation rentals

    Explore 20 vacation rentals in Shelbyville

  • Nightly prices starting at

    Shelbyville vacation rentals start at $140 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Shelbyville vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shelbyville rentals

  • 4.9 Average rating

    Shelbyville stays are highly rated by guests—averaging 4.9 out of 5!