Vacation rentals in Oldham County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oldham County

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

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Guest favorite

Home in La Grange

5 out of 5 average rating, 227 reviews

Your Romantic Cabin with Hot tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown LaGrange. Guests have the entire home with front and back porch overlooking the big backyard. The master bedroom has a queen bed and the second bedroom has a full bed. The kitchen is fully equipped and ready for some country cooking. The fire pit is located in the back yard ready for you or you can use the gas fire pit just steps from the hot tub. The hot tub is ready for guests with a view of stars!

Guest favorite

Guesthouse in Prospect

5 out of 5 average rating, 65 reviews

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 double bed 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!

Guest favorite

Condo in La Grange

4.98 out of 5 average rating, 65 reviews

The Beje (‘bay-hay’)-King Bed-Coffee Bar

Not corporately owned, our former residence and one and only Airbnb. The Beje is a second-floor condo offering security, privacy and quality in a prime location. We operate a weekday insurance office downstairs which is protected by ADT. Located in historic downtown LaGrange, you're just a short walk to coffee, restaurants, parks, antique shopping, Farmer's market and fabulous Main Street where the train rolls right down the middle. Ideal for single travelers, couples and small families.

Guest favorite

Home in Crestwood

5 out of 5 average rating, 32 reviews

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!

Guest favorite

Home in Louisville

4.98 out of 5 average rating, 104 reviews

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, and just 15 minutes from Valhalla Country Club, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

Guest favorite

Cottage in Prospect

4.98 out of 5 average rating, 111 reviews

Cozy Cottage on Famous Kentucky Farm

A cozy cottage house on Foxhollow Farm, featured on Season 16 of Bravo's Top Chef, a grassfed beef farm just 20 minutes from downtown Louisville. Enjoy the serene landscape of a 1,300-acre family farm during your stay in The Fox Den Cottage, surrounded by horses, cattle set to pasture, and the natural sounds of chickens and roosters. Just 25 minutes from Churchill Downs, it's perfect for Oaks/Derby or a relaxing visit to the Bluegrass State to enjoy Louisville’s treasures, like bourbon.

Guest favorite

Tiny home in La Grange

4.98 out of 5 average rating, 190 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

Guest favorite

Guest suite in Louisville

4.95 out of 5 average rating, 152 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our guest suite offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Guest favorite

Home in La Grange

4.9 out of 5 average rating, 73 reviews

Caboose Cottage

Historic 3 bed, 1 bath farmhouse within walking distance of downtown LaGrange & The Railroad Museum. Secluded on a 1.5 acre lot with a fenced in backyard, fire pit, private patio & perfect view of the CSX train line rolling into Main Street. A few minutes walk to local gift shops, restaurants & coffeehouse. 25 minutes from Louisville International Airport & downtown Louisville. Less than 15 minutes to the home of Jefferson's Reserve Bourbon, Kentucky Artisan Distillery.

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 199 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 121 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Guest favorite

Cabin in La Grange

4.98 out of 5 average rating, 163 reviews

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.