House vacation rentals in Oldham County

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Top-rated house rentals in Oldham County

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Top guest favorite

A modern living area is displayed, featuring a light gray sofa adorned with various pillows. A rustic coffee table sits at the center, surrounded by natural light from two large windows with wooden blinds. Dark curtains frame the windows, complementing the warm wood flooring.

Home in La Grange

5 out of 5 average rating, 34 reviews

5 Star Luxury Sweet Retreat Wheelchair Acessible

Former bakery completely renovated into a "sweet retreat" for your visit to La Grange, the Kindness Capital of Kentucky! Just steps from the only railroad that still runs down an active Main Street. Wheelchair accessible—two bedrooms, two tiled baths, sleeps 8. Historic Downtown La Grange boasts unique shops, restaurants, a train viewing tower with over 30 trains/day, parks and the Alley Loop (a fun interactive art walk). Nearby horse farms, Churchill Downs, Bourbon Trail, 20 mins to Louisville.

Top guest favorite

The exterior of Deerview Cabin features a wooden porch with a welcome sign, surrounded by hanging plants and potted greenery. A rustic metal roof contrasts with the natural wood siding. Chairs are placed on the porch, inviting relaxation in a serene rural setting.

Home in La Grange

5 out of 5 average rating, 245 reviews

Romance country getaway 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!

Top guest favorite

Home in Prospect

5 out of 5 average rating, 116 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

Top guest favorite

Home in La Grange

4.95 out of 5 average rating, 78 reviews

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

“The Lady Jinx” is a newly 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!

Top guest favorite

The open-concept living area features warm wood flooring, comfortable seating, and a flat-screen TV positioned above a cozy fireplace. Two large windows allow natural light to flood the space, complemented by neutral walls and wooden beams overhead. A stylish console table adds functional décor near the entrance.

Home in Crestwood

5 out of 5 average rating, 65 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!

Top guest favorite

Home in La Grange

4.96 out of 5 average rating, 24 reviews

Barn + House | 30 Acres | Pickleball | Basketball

This is the perfect spot for your group. Sleeps 14! 4 King beds 3 queen beds! Outdoor amenities: +30 acres with trails + 2 Pickleball Courts +Full court Basketball +Soccer Field +Playground +Springless Trampoline +Fire pit +Grill +Corn hole Game Barn features +Pool Table +Ping Pong Table +Poker Table +Arcade: Pinball, head to head, retro games +2 Smart TVs +Foosball +Loft area +Starlink internet House Amenities: +2 Living Rooms +Large Deck +2 Kitchens +Kid-friendly + 3 Full Bathrooms

Top guest favorite

A spacious living area features a large sectional sofa adorned with decorative pillows, a round coffee table, and a cozy armchair. A ceiling fan hangs above, and wooden wall decor adds character. The dining area is visible in the background, inviting communal gatherings.

Home in Prospect

5 out of 5 average rating, 39 reviews

Pet-Friendly, Shops, Bourbon Trail, Downtown, Golf

Welcome to your fall escape in the heart of Norton Commons! Watch Hill Manor is the perfect gateway to explore downtown Louisville, the Bourbon Trail, and rolling horse country. Enjoy crisp autumn days with a stroll to local shops, great dining, and community events right outside your door. The location also provides easy access to distilleries, scenic horse farms, golf courses, and seasonal activities like festivals and foliage tours. Book your memorable Kentucky getaway today!

Superhost

The exterior of a modern single-story home is depicted, featuring a stone façade and a welcoming front porch. A white picket fence stands prominently, along with a concrete driveway providing parking. Lush greenery surrounds the house, enhancing the tranquil ambiance.

Home in La Grange

4.9 out of 5 average rating, 115 reviews

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.

Guest favorite

The historic home is depicted in a serene landscape, featuring a combination of warm colors. A welcoming porch stretches across the front, complemented by multiple windows and a distinctive roofline. Lush greenery surrounds the property, enhancing its inviting presence.

Home in Crestwood

4.97 out of 5 average rating, 34 reviews

The Yellow House @ Floydsburg

This Historic Home sits on 2.5 acres of a gorgeous park like setting in a convenient location! Your travel group will be comfortable in this spacious and unique property. Perfect for family vacations or guests coming in town for weddings as 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!

Guest favorite

The living area features a spacious sectional sofa arranged around a round wooden coffee table. Natural light filters through sheer curtains, illuminating the room. Decorative shelves are mounted on the walls, and a ceiling fan is present for comfort.

Home in Crestwood

4.91 out of 5 average rating, 113 reviews

12 Guest/Top Area /Families/Park

Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

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

4.97 out of 5 average rating, 99 reviews

The Squirrel's Nest - 3 bedroom house 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 FRP-LaGrange Quarry water park. The back patio overlooks the woods where you can watch deer, turkey & the squirrels play! The master bedroom has a queen bed, the second & third bedrooms have full beds. The kitchen is fully equipped. No pets. No parties, no events.

Top guest favorite

An entryway features warm wooden flooring and natural light from a window with blinds. A welcoming bench with a decorative pillow sits against the wall. A round woven wall hanging adds texture beside a lamp on a small side table, with a staircase visible in the background.

Home in Pewee Valley

4.98 out of 5 average rating, 169 reviews

Bourbon Trail*Pewee Valley *HOT TUB

Welcome to the Bourbon Bungalow, a tastefully restored farmhouse on the famous Kentucky Bourbon Trail. This southern retreat is on the outskirts of Louisville in the quaint city of Pewee Valley. A short drive to some of the states most sought after locations such as Churchill Downs, bourbon distilleries, horse parks, caves, Shelbyville, Bardstown, & more! The Bourbon trail is waiting for you!