Family-friendly holiday rentals in Crestwood

Cozy Cottage on Famous Kentucky Farm

Experience the beauty of Kentucky farmland with hundreds of acres to explore, including our nature trail where you might spot our beef cattle and horses. Relax on the charming front porch, watch the fireflies, and soak in the peaceful atmosphere. Our cottage features a homey and cozy feeling with two spacious bedrooms: a master bedroom with a comfortable queen bed and a second bedroom with a full-size bed, perfect for families or couples. Perfect to explore the events like the Kentucky Derby.

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

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.

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

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

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!

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.