Holiday houses 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.

Location · Value · Layout

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

Location · Family · Accuracy

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country-neighboring horses graze in adjacent fields. Queen bed upstairs, converted sofa queen in loft. Air bed also available. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

Location · Value · Backyard

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!

Value · Family · View

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.

Location · Family · Cleanliness

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!

Family · Value · Long stay

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

Location · Value · Condition

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.

Family · Location · Indoor spaces

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.

Value · Location · View

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 99 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

Value · Family · Decor

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

Family · Value · Quiet

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....

Location · Value · Indoor spaces