House holiday rentals in Oldham County

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Top-rated house rentals in Oldham County

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

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Top guest favourite

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.

FamilyLocationCheck-in

4.93 out of 5 average rating, 42 reviews

Top guest favourite

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.

Home in La Grange

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.

ValueFamilyAccess

4.98 out of 5 average rating, 66 reviews

Guest favourite

Home in Prospect

The Riverside Retreat - Your Coastal Getaway

Take it easy at this unique and tranquil getaway, perfectly situated with the Ohio River right in your backyard. Relax on the spacious back deck and enjoy stunning river views while unwinding in a peaceful setting. This home has been recently updated with a refreshed kitchen, flooring, modern lighting, updated bedrooms, and a renovated shower, making it a comfortable and inviting retreat for the duration of your stay. The Riverside Retreat is the perfect place to recharge and enjoy the scenery

LocationFamilyAmenities

4.86 out of 5 average rating, 148 reviews

Top guest favourite

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

Romantic country getaway with hot tub

Deerview Cabin is a completely renovated 1940's farm house 10 minutes from historic 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!

LocationValuePool

5.0 out of 5 average rating, 268 reviews

Guest favourite

Home in Buckner

Exclusive Buckner retreat w/ theater & game room!

Welcome to this inviting 3-bedroom, 3-bath Buckner home, ideal for families and groups seeking relaxation and fun. This 1,790 sq ft retreat features multiple entertainment areas: a theater-style family room, a game room with bar, and a dedicated basement gym. The open kitchen is fully equipped, paired with a cozy second-floor living room with fireplace and dining area. Unwind in the private backyard, with ample parking, full-home WiFi, and easy access to Buckner and Louisville attractions.

ValueLocationOutdoor spaces

5.0 out of 5 average rating, 7 reviews

Top guest favourite

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!

FamilyLocationCheck-in

5.0 out of 5 average rating, 96 reviews

Top guest favourite

The living room features a classic design with rich green walls and a mix of hardwood and patterned flooring. Two ornate armchairs are positioned opposite a dark wood coffee table, with a leather sofa off to the side. Large windows allow natural light to fill the space.

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!

ValueFamilyHeating

4.96 out of 5 average rating, 105 reviews

Guest favourite

A brick ranch-style house is presented, featuring a welcoming entrance with a set of stairs leading to the front door. Large windows are visible, allowing natural light to brighten the façade. A well-maintained lawn with green grass surrounds the property, enhancing the home’s curb appeal.

Home in La Grange

The Hoffman House - LaGrange, KY

The Hoffman House is a quaint brick ranch located just 3/4 of a mile from downtown historic LaGrange, Kentucky. With three bedrooms and one bathroom, the Hoffman House provides comfortable accommodations for up to 6 people. Pets allowed with pre-approval only and will incur additional fee. The City of LaGrange charges an additional 3% transient room tax on short term rentals. After booking I will send a resolution request for the taxes. Example: $500 stay will result in $15 fee.

ValueLocationKitchen

4.82 out of 5 average rating, 39 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.

FamilyLocationWifi

4.91 out of 5 average rating, 142 reviews

Top guest favourite

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.

LocationFamilyCondition

4.97 out of 5 average rating, 116 reviews

Top guest favourite

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!

FamilyLocationIndoor spaces

4.98 out of 5 average rating, 52 reviews

Top guest favourite

A stylish living area features a modern gray sofa accompanied by two blue accent chairs. A large flat-screen TV is mounted above a black fireplace. Natural light enters through multiple windows, which frame views of the surrounding greenery, enhancing the room's serene ambiance.

Home in Louisville

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, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

LocationFamilyCheck-in

4.98 out of 5 average rating, 138 reviews