Holiday rentals with outdoor seating in Oldham County

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.

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!

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 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 !

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.

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!

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

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.

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.

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.)

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.

Little Blue Cottage on Main Street, La Grange KY

Our quaint blue cottage right on Main Street gives you a front row view to one of the last main rail lines through a downtown area in America! -Walking distance to multiple restaurants, coffee shops, and antique stores -10 minutes from Jefferson's Reserve Distillery -25 minutes from downtown Louisville - Central to the bourbon trail with over 20 distilleries less than an hour away - On the Alley Loop as showcased on HGTV