Cottage vacation rentals in Shelbyville

4.98 out of 5 average rating, 277 reviews

A porch overlooks the serene Kentucky River, featuring a wood breakfast bar with counter stools. Rocking chairs provide a cozy seating area, framed by lush greenery and views of the river's banks. Sunlight filters through the trees, enhancing the tranquil setting.

Cottage in Wilmore

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

4.97 out of 5 average rating, 205 reviews

Luxury Retreat with Hot Tub

Welcome to Four Seasons Cottage on the Bourbon Trail! This charming property is located in a peaceful vacation community, just a short walk from the seasonal pool. Featuring 2 bedrooms, a fully equipped kitchen, and cozy living room with a fireplace, this cottage is perfect for a family getaway or a couples retreat. Enjoy the large deck with a hot tub and BBQ, as well as access to nearby hiking trails and attractions. Cottage 37 sits on a ridge that overlooks the 3,050-acre Taylorsville Lake.

4.97 out of 5 average rating, 145 reviews

A cozy living area is presented with a television mounted on the wall. A black leather sofa faces a small wooden coffee table and two armchairs. Natural light filters through the windows, complemented by patterned curtains, creating a warm atmosphere.

Cottage in Salvisa

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

4.94 out of 5 average rating, 216 reviews

An expansive deck presents scenic views of Herrington Lake, bordered by trees for a natural ambiance. Outdoor seating with a table invites relaxation, while the gentle waters below contribute to a peaceful setting.

Cottage in Harrodsburg

Paradise Cottage Enjoy lake Views and Lake Access!

Relax and enjoy! Great Herrington Lake views with lake access at Paradise Cottage! Peaceful private setting on one of the most beautiful parts of the lake. Located Mins from Multiple marinas, Bourbon trail, golf courses, Centre College/Asbury University events. 3 bedrooms, 5 beds, 2 full bathrooms, washer/dryer, newly remodeled. Sleeps 9. Includes: wi-fi, Hulu, 2 TVs, multiple decks, covered side patio, fire pit, gas grill, corn hole, kayaks and lily pad included with stay! Four parking spaces!

4.96 out of 5 average rating, 193 reviews

The exterior showcases a charming white house with large windows adorned with string lights, offering a glimpse of the interior space. A wooden deck extends out front, while a covered patio area is visible to the side, surrounded by lush greenery.

Cottage in Irish Hill

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

4.98 out of 5 average rating, 125 reviews

A cottage is nestled among lush greenery, featuring a well-maintained lawn and vibrant flower beds. The exterior includes classic shutters and a prominent stone chimney, surrounded by mature trees that provide ample shade.

Cottage in Prospect

Cozy Cottage on Famous Kentucky Farm

Experience the beauty of Kentucky farmland with hundreds of acres to explore, including our nature trail where you might spot our beef cattle and horses. Relax on the charming front porch, watch the fireflies, and soak in the peaceful atmosphere. Our cottage features a homey and cozy feeling with two spacious bedrooms: a master bedroom with a comfortable queen bed and a second bedroom with a full-size bed, perfect for families or couples. Perfect to explore the events like the Kentucky Derby.

4.95 out of 5 average rating, 134 reviews

Cottage in Lawrenceburg

Bourbon Barrel Cottages 2 Ky Bourbon Trail HOT TUB

Leave the Cleaning to Us – Your Bourbon Country Escape Awaits! Kick back, relax, and unwind in a stylish, serene retreat nestled in the heart of Kentucky’s Bourbon Country. Welcome to Bourbon Barrel Cottages, where nature, comfort, and convenience come together. Each of our five private two-bedroom cottages sits on its own two-acre lot, surrounded by wildlife and natural beauty—perfect for couples, friends traveling together, or anyone seeking peace and privacy. You'll Love Staying with Us!

4.99 out of 5 average rating, 441 reviews

The charming yellow cottage features a covered front porch with two black chairs, inviting relaxation. Neatly trimmed hedges line the walkway, leading up to the front door, which is adorned with a decorative wreath. A spacious lawn and a clear blue sky enhance the warm appearance.

Cottage in Bardstown

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

A two-story cottage is situated against a lush green backdrop. The exterior features light-colored siding, a covered porch, and multiple windows that allow natural light. A well-maintained lawn surrounds the home, enhancing the inviting appearance of the property.

4.94 out of 5 average rating, 179 reviews

The Gathering Place

The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

Cottage in Spencer County

Aerial view captures Taylorsville Lake, surrounded by lush greenery and autumn foliage. The winding shoreline is visible alongside the marina with several boat docks. The community road runs beside the scenic landscape, providing a clear view of the serene water and rolling hills.

4.92 out of 5 average rating, 159 reviews

Peaceful Cottage Minutes from Lake Access

Welcome to our fully stocked getaway! In this 2 bed, 2 bath cottage you will find everything you need to have a relaxing and fun vacation. You will love the deck with scenic views of Taylorsville Lake, and a hot tub with privacy fence. Lake access is less than a 5 minute drive, and there is a community pool just down the road when in season, and other community amenities you can enjoy. We are excited to host you here and hope that you will enjoy this place as much as we have!

4.99 out of 5 average rating, 225 reviews

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

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.

4.95 out of 5 average rating, 151 reviews

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Popular amenities for Shelbyville cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A two-story cottage features a welcoming red front door and a spacious porch with wooden steps leading up. The exterior showcases grey siding surrounded by lush green grass and shrubbery, while a colorful community playground is visible in the background.

4.77 out of 5 average rating, 145 reviews

Anchor Rental

4.95 out of 5 average rating, 74 reviews

The living room showcases a stylish design with emerald green sofas and a round coffee table atop a geometric rug. A decorative fireplace and vintage record player are featured, alongside a striking mural of a horse. Natural light complements the brick wall and potted plants.

Cottage in Shelbyville

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tu

The living area features cozy seating arrangements, including two sofas, one with a throw blanket draped across it. A stone fireplace acts as a focal point under a mounted television. Light filters in through a window adorned with sheer curtains, enhancing the warm atmosphere.

4.69 out of 5 average rating, 78 reviews

"On the Rocks" Bourbon Trail Getaway

5 out of 5 average rating, 46 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

New place to stay

Weekend Getaway | Lake Access | Hot Tub | Bourbon

Cottage in Spencer County

A single-story cottage is framed by lush greenery, featuring a welcoming front porch supported by decorative pillars. Manicured shrubs and trees surround the home, creating a serene atmosphere. The roof is gently sloped, and a grassy area adds to the inviting outdoor space.

5 out of 5 average rating, 24 reviews

LAKE COTTAGE, near Louisville & the Bourbon Trail

A living area features comfortable seating arranged around a wooden coffee table. A stone fireplace with an electric insert is positioned beneath a flat-screen television mounted on the wall. The warm red walls create a cozy backdrop, and kitchen facilities are visible in the background.

4.99 out of 5 average rating, 142 reviews

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

Superhost

A single-story cottage is presented with a gray exterior and a welcoming red front door. Lush greenery surrounds the property, with well-kept shrubs and a manicured lawn. Large windows allow natural light into the interior, enhancing the inviting appearance of the home.

4.82 out of 5 average rating, 138 reviews

Mint Julep Cottage near Louisville & Bourbon Trail

Pet-friendly cottage rentals

4.97 out of 5 average rating, 78 reviews

An inviting living space features a large sectional sofa adorned with decorative pillows. A patterned area rug lies beneath a central coffee table. Natural light filters through several windows, and wooden walls add warmth to the environment. A dining area with white chairs is visible in the background.

Cottage in Willisburg

A Romantic Getaway on the Bourbon Trail

4.87 out of 5 average rating, 179 reviews

A charming cottage is set on a spacious lawn, framed by manicured shrubs and trees. The exterior features a traditional design with white siding and dark shutters. A gravel driveway leads to the home, providing ample parking space.

Cottage in Prospect

Cottage in Louisville,KY on Scenic River Rd

A charming two-bedroom cottage is displayed, featuring a combination of gray siding and a peaked roof. The front porch is accessible via a small set of steps, surrounded by manicured grass and shrubs. Nearby trees provide a touch of greenery against a clear blue sky.

4.91 out of 5 average rating, 137 reviews

Best view of the lake two bed two bath cottage #4

The cottage exterior showcases a welcoming front porch with a vibrant red door. Lush greenery and flowering plants surround the entrance, set against a clear blue sky. The single-story structure features a gabled roof and neatly maintained landscaping.

4.85 out of 5 average rating, 117 reviews

Shore Thing Bourbon Trail Lodging #20

Superhost

An open-plan kitchen and living area features a map of the United States as a focal point above a decorative bar table with two high chairs. A deep red armchair adds a cozy touch, while stainless steel appliances and a stylish stove are visible in the background.

Cottage in New Haven

5 out of 5 average rating, 4 reviews

Mile Back Hide-Away

A charming cottage exterior is showcased with a colorful front door. Lush greenery frames the entrance, and large windows allow natural light to fill the space. The well-maintained pathway leads to the welcoming porch, set against a clear blue sky.

4.71 out of 5 average rating, 178 reviews

Get Away From It All

4.73 out of 5 average rating, 320 reviews

The exterior of a historic red home features a distinct black-trimmed door and a green roof. A garden of blooming daffodils surrounds the base, providing a vibrant contrast to the building, while a wooden fence encapsulates the property, enhancing the charm of the setting.

Cottage in Bardstown

Bourbon Oak Smokehouse Cottage

4.96 out of 5 average rating, 69 reviews

A charming cottage is set within a rural landscape, surrounded by trees and open fields. A cow grazes nearby, and large windows invite natural light into the living space. The entrance features a welcoming porch area with seating and a clear view of the tranquil surroundings.

Cottage in Lexington

Springwood Cottage in the heart of the Bluegrass.

Private cottage rentals

4.97 out of 5 average rating, 30 reviews

An overhead view of a living area showcases a light blue wall with a ceiling fan above a beige sectional sofa. A patterned area rug lies beneath, with a wooden coffee table at the center. Natural light enters through glass doors leading to an outdoor space.

Cottage in Shelbyville

The Farm cottage

4.86 out of 5 average rating, 341 reviews

A bright living room is furnished with a gray sofa and two blue armchairs. A glass coffee table is centered on a colorful area rug. A flat-screen TV sits on a wooden console, and a bookshelf is visible, filled with various books. Natural light enters through multiple windows.

Cottage in Germantown

Tyler Park Cottage in the Highlands

4.99 out of 5 average rating, 80 reviews

The front of the house features a welcoming porch with light-colored Adirondack chairs. Large windows allow plenty of natural light inside. The structure is accented by a decorative window at the peak and is surrounded by a spacious deck, framed by trees and clear blue skies.

Cottage in Floyds Knobs

Tranquil setting with breathtaking views

Cottage in Jeffersonville

The exterior of a riverfront home is visible, featuring a large deck with several adirondack chairs arranged around a fire pit. A grill is positioned nearby. Lush green grass surrounds the property, with trees in the background offering a natural setting.

4.91 out of 5 average rating, 87 reviews

Riverfront 2BR Home w/ Deck, Huge Yard & Driveway

A white picket fence encircles a garden area filled with vibrant flowers, including orange lilies and purple blooms. A wooden sign reading 'Bikers Welcome' leans against the fence. Decorative pots hang nearby, enhancing the inviting exterior of the cottage.

Cottage in Bardstown

4.89 out of 5 average rating, 418 reviews

Bardstown Coppersmith Cottage

4.96 out of 5 average rating, 69 reviews

An open living area features a vibrant area rug with swirling colors, complemented by a navy blue sectional and a light wood floor. A flat-screen television is mounted on the wall, while natural light fills the space through large windows, illuminating cozy seating areas.

Cottage in Harrodsburg

Cozy Tree House @ Herrington Lake near Lexington

4.99 out of 5 average rating, 156 reviews

A cozy living room features a grey sofa adorned with decorative pillows. A wooden coffee table is situated in front, with storage compartments. Two patterned chairs are positioned nearby, and a bookshelf displays various decorative items. Soft lighting is provided by a standing lamp.

Cottage in Louisville

Derby City