Vacation rentals in Oldham County

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Top-rated vacation rentals in Oldham County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

An open kitchen and dining area features modern appliances and a spacious dining table with multiple chairs. Sunlight pours through large windows, offering views of the outdoor landscape. A cozy seating area with neutral-colored cushions and decorative pillows is positioned nearby.

Home in Crestwood

Garden House, a private getaway

Welcome to "The Garden House" a serene retreat nestled on 9 acres in Crestwood. This charming home offers a tranquil escape just 20 minutes from downtown Louisville. This home is a 4-bedroom sanctuary, meticulously renovated to offer modern comforts. Guests can enjoy premium amenities including solar power, Tempurpedic mattresses, and soft bedding for a great night's sleep. Whether you are planning a wedding, exploring the Bourbon Trail, or seeking a getaway, it promises to be a memorable stay.

FamilyLocationAccess

4.93 out of 5 average rating, 40 reviews

Top guest favorite

A cozy front porch features woven chairs arranged around a small table, inviting relaxation. Lush green ferns are placed in terracotta pots, complementing the rustic wooden beams and the log cabin's natural surroundings.

Cabin in La Grange

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

FamilyLocationBackyard

4.97 out of 5 average rating, 138 reviews

Top guest favorite

A charming two-story brick guest house is set against a lush green lawn. The exterior features large windows and a welcoming front porch with two white chairs. A gently curving driveway leads to the entrance, framed by manicured shrubs and a nearby tree.

Guesthouse in Prospect

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country-neighboring horses graze in adjacent fields. Queen bed upstairs, converted sofa queen in loft. Air bed also available. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

FamilyValueAccess

5.0 out of 5 average rating, 134 reviews

Top guest favorite

Home in La Grange

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

If you're choosing the house for the group, this is the place everyone thanks you for later. Five king beds, a year-round heated saltwater pool, covered hot tub, two game rooms, and a chef's kitchen give up to 12 guests room to connect and room to retreat. Set on 3.75 private acres with total privacy, just 20 minutes from Louisville, bourbon trail, and Churchill Downs. Sleeps 12 comfortably. Even the teenagers come downstairs. And the WiFi actually works. Built for Joy. Made for Generations.

ValueLocationHot tub

4.99 out of 5 average rating, 97 reviews

Top guest favorite

An open-concept living area features a cozy sofa and armchair, with light-colored walls and wooden beams above. The modern kitchen, equipped with stainless steel appliances and a spacious island, is complemented by bar seating and a view of the outdoors through a window.

Home in Crestwood

Briar Creek Cottage

Welcome to this cozy 2-bed, 2-bath cottage, just 25 minutes from the Louisville Airport & conveniently close to the Kentucky Bourbon Trail. Recently renovated, this cottage is nestled in a peacefully wooded lot with modern amenities. The primary suite includes a queen bed, an en suite bathroom, and an optional pack-n-play. The second bedroom also features a queen bed and adjacent bath. Perfect for a tranquil getaway or exploring the Kentucky Bourbon Trail. Book now for a charming retreat!

FamilyLocationParking

5.0 out of 5 average rating, 94 reviews

Top guest favorite

A cozy living room features a leather chesterfield sofa, complemented by an armchair and a wooden coffee table. Wall decor includes animal artwork and mirrors. Natural light filters through sheer curtains, illuminating the warm wood floor and enhancing the room's classic design.

Home in La Grange

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

“The Lady Jinx” is a renovated 3 BR/2.5 Bath, Princess Anne-style Home built in 1895. This 2-story has tons of character from the detailed wood trim to the stain glass windows to the original interior doors to the gorgeous wood floors. The home is located in downtown La Grange, the only town in America that has an active train running along it’s Main Street, & is within walking distance to restaurants, shopping boutiques, museums, parks and entertainment with being only one block away!

FamilyLocationHospitality

4.96 out of 5 average rating, 102 reviews

Top guest favorite

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 home in La Grange

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

ValueFamilyAir conditioning

4.99 out of 5 average rating, 274 reviews

Superhost

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

FamilyValueSleep quality

4.91 out of 5 average rating, 142 reviews

Top guest favorite

The exterior of the home features brick siding with white trim and dark blue shutters. Lush green grass surrounds the property, complemented by mature trees. A set of steps leads to the front door, which is framed by small hedges on either side.

Home in La Grange

The Squirrel's Nest - 3 bed/2 bath with hot tub

Welcome to the Squirrel's 🐿️ Nest where you can relax and enjoy the country! Only 5 mins from historic downtown LaGrange, 20 mins from Louisville-home of the Kentucky Derby and next door is the Bluegrass Springs where you can swim/float in the old quarry. The back patio overlooks the woods where you can watch deer, turkey & the squirrels 🐿️ play! Or just relax in the hot tub! All the bedrooms have queen beds. The kitchen is fully equipped. No pets. No parties, no events.

FamilyLocationSleep quality

4.97 out of 5 average rating, 113 reviews

Top guest favorite

An inviting sitting area features two curved sofas facing a small circular table. A built-in bookcase with decorative items lines one wall. Natural light floods the space through large windows, highlighting the wood flooring and elegant decor.

Home in Crestwood

The Yellow House @ Floydsburg

This Historic Home sits on 2.5 acres of a gorgeous park like setting in a convenient location! Perfect for family vacations visits to Louisville for Kentucky Derby, Bourbon Trail, or guests coming in town for weddings. This property is close to many different wedding venues in the area, including Duncan Memorial Chapel, Bradshaw Duncan House, & Yew Dell Gardens, and only 25 minutes to downtown Louisville. Come relax & enjoy your Home Away from Home!

FamilyLocationQuiet

4.98 out of 5 average rating, 51 reviews

Top guest favorite

A spacious great room features reclaimed barn wood flooring and a stone fireplace as its focal point. Large windows allow natural light to fill the space, complemented by rustic furniture, including comfortable armchairs and a wooden coffee table. Warm tones create a cozy gathering area.

Farm stay in Pendleton

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 99 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

FamilyValueNearby

4.99 out of 5 average rating, 156 reviews

Top guest favorite

A cozy living area features a large sectional sofa and a colorful area rug. Natural light enters through two windows, illuminating the room. A ceiling fan enhances airflow, and decorative elements include a shelf with framed artwork.

Home in La Grange

Little Blue Cottage on Main Street, La Grange KY

Our quaint blue cottage right on Main Street gives you a front row view to one of the last main rail lines through a downtown area in America! -Walking distance to multiple restaurants, coffee shops, and antique stores -10 minutes from Jefferson's Reserve Distillery -25 minutes from downtown Louisville - Central to the bourbon trail with over 20 distilleries less than an hour away - On the Alley Loop as showcased on HGTV

FamilyValueParking

4.96 out of 5 average rating, 237 reviews