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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Guest favorite

Home in La Grange

5.0 out of 5 average rating, 212 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!

Oct 10 – 17

G$36,168 GYD per night

Guest favorite

Guesthouse in Prospect

5.0 out of 5 average rating, 29 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, brand new sofas/pull out beds upstairs and downstairs. 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!

Sep 7 – 14

G$24,756 GYD per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 34 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.

Nov 27 – Dec 4

G$27,802 GYD per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 119 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 newly renovated space 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!

Dec 23 – 30

G$22,124 GYD per night

Guest favorite

Home in Prospect

4.94 out of 5 average rating, 209 reviews

The River House

Welcome to a beautifully maintained home on the River. This home provides an open concept perfect for family or business gatherings. 4 private bedrooms with several spaces to add sleeping areas for additional guests. The elevator from the basement to the top floor provides easy access for our senior visitors and other guests. Three full baths will keep anyone from fighting over shower time and three levels of patios will provide your preferred view of the river. Welcome to relaxation.

Jan 30 – Feb 6

G$57,926 GYD per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 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

Dec 7 – 14

G$20,441 GYD per night

Guest favorite

Apartment in Pewee Valley

5.0 out of 5 average rating, 22 reviews

Loft in Pewee Valley

Welcome to our charming Pewee Valley loft! This tastefully decorated 2-bedroom, 1 bathroom space is an inviting retreat for your next getaway. Nestled in a peaceful town, it offers a perfect blend of comfort and serenity. Lounge in the cozy living area or enjoy a cup of coffee on the private balcony. Conveniently located near local attractions and with easy access to nearby cities, this hidden gem is ready to make your stay unforgettable. Book now and experience the charm firsthand!

Jul 6 – 13

G$24,869 GYD per night

Guest favorite

Home in La Grange

4.91 out of 5 average rating, 47 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.

Oct 6 – 13

G$30,666 GYD per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 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.

Jun 21 – 28

G$29,458 GYD per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 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.)

Aug 22 – 29

G$26,034 GYD per night

Guest favorite

Cabin in La Grange

4.98 out of 5 average rating, 156 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.

Jun 20 – 27

G$71,119 GYD per night

Guest favorite

Loft in Charlestown

4.93 out of 5 average rating, 42 reviews

Cozy hideaway on Yankee creek.

In the country, yet close to the city. You’ll love our cozy hideaway in the beautiful Indiana farmland. Situated in between the small towns of Charlestown and New Washington.You’ll be only minutes away from beautiful hiking at Charlestown State Park or head up the Ohio river scenic by-way (HWY 62) to Clifty Falls State Park in Madison, Indiana. This area is about 20 minutes to the east bridge(Lewis and Clark bridge)to Louisville, Kentucky.

Mar 1 – 8

G$23,000 GYD per night