Holiday rentals with a patio in Oldham County

A spacious dining area features a large wooden table surrounded by four modern chairs. Natural light streams in through two windows adorned with blinds, highlighting the earthy tones of the accent wall. Decor includes simple art pieces and a decorative bowl on the table.

4.98 out of 5 average rating, 54 reviews

5 Stars Sweet Retreat Wheelchair Accessible

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.

4.91 out of 5 average rating, 33 reviews

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.

5 out of 5 average rating, 85 reviews

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!

5 out of 5 average rating, 125 reviews

An outdoor seating area is displayed, featuring two white armchairs and a stone-top coffee table, arranged on a green and white striped rug. String lights illuminate the space, which is bordered by tall green shrubs and a wooden fence.

Home in Prospect

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Superhost

4.9 out of 5 average rating, 134 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.

4.93 out of 5 average rating, 71 reviews

A well-appointed studio apartment displays a gray sofa draped with a soft throw, complemented by a yellow decorative pillow. The space features wall art, a wooden coffee table with leaf design, and a cozy yellow quilted bed visible in the background.

Flat in Charlestown

Cozy Hideaway

You will love The Cozy Hideaway! A great place to rest and relax, also enjoy this great central location to explore Southern Indiana! Only 20 minutes to Jeffersonville & 20 minutes to the Lewis and Clark bridge to Louisville. Situated in between Charlestown and New Washington. Very near beautiful hiking at Charlestown State Park or head up the Ohio river scenic by-way to Clifty Falls State Park in Madison, Indiana. We are dog friendly , only one dog and a pet fee required.

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.

4.97 out of 5 average rating, 106 reviews

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.

4.95 out of 5 average rating, 91 reviews

The exterior of a modern brick house is framed by mature trees with autumn leaves. A well-maintained lawn extends in front of the house, which features multiple large windows allowing natural light to enter. A gravel driveway leads up to the welcoming entrance.

Guest suite in Crestwood

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

4.87 out of 5 average rating, 69 reviews

A serene view of a quiet creek is presented, with lush greenery lining the banks. A boat is docked at a wooden pier, providing access to the water. Sunlight filters through the trees, casting dappled light on the water's surface.

Holiday home in Prospect

Harrods Hideaway waterfront stay above the tavern

If you love the nightlife and water we have the place for you! It has a beautiful back deck overlooking the creek. Boat docks are available at no extra charge. We are right upstairs from Harrods Creek Tavern, which is a great place to hang out with the locals. Music is heard until late at night and you can play a game of pool, darts, scratchoffs, and we now have skilled games. You can enjoy a large selection of spirits and we even have food available from 11am-2am.

5 out of 5 average rating, 9 reviews

A modern home with a welcoming façade features a symmetrical design, a covered porch, and a manicured lawn. Neat hedges and trees surround the front yard, with a clear walkway leading to the entrance. The sky above displays a calm blue, enhancing the overall appeal.

Home in Prospect

Anemone Estate – Private Luxury Staycation Retreat

Welcome to your private escape in Prospect—where comfort meets connection. Whether you’re gathering with friends, celebrating something special, or simply stepping away from the everyday, this home was designed to bring people together in a relaxed, upscale setting just minutes from Louisville. ✨ Perfect For: * Family gatherings * Girls/guys weekends * Wedding stays * Staycations * Small group retreats * Traveling Nurses * Corporate Stays * Extended Visits

4.98 out of 5 average rating, 45 reviews

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!

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.