House holiday rentals in Oldham County

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Top-rated house rentals in Oldham County

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Top guest favourite

Home in La Grange

5 out of 5 average rating, 23 reviews

The Sweet Retreat Wheelchair Access Historic Home

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 6. 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.

Top guest favourite

Home in La Grange

5 out of 5 average rating, 240 reviews

Romance country getaway with hot tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown 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!

Top guest favourite

Home in Prospect

5 out of 5 average rating, 108 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

Top guest favourite

Home in La Grange

4.94 out of 5 average rating, 72 reviews

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

“The Lady Jinx” is a newly 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!

Superhost

Home in La Grange

4.88 out of 5 average rating, 17 reviews

Remodeled 50s Home in Quaint Downtown LaGrange

Fantastic location, where you can walk to quaint shops and restaurants in downtown LaGrange. We recently remodeled this 50s home from top to bottom, and it has everything you need to feel at home. The house is located close enough to the train tracks on Main Street that you can walk to see the train, but we rarely can hear it go by. Close proximity to I-71, and about 20 miles from Louisville. LaGrange has its own unique charm, while still being close enough to visit and enjoy Louisville.

Top guest favourite

Home in La Grange

4.98 out of 5 average rating, 54 reviews

Where generations come to connect | Pool | Games

✨ 8 ft. deep-end saltwater pool, safety autocover, and optional *heat; ✨ Outdoor paradise: 6 lux lounge chairs, al fresco dining for 12, charcoal grill, hammock, cornhole, bucket golf, space to play ✨ Hot tub, Karaoke, Fire pit, garage games (pool, foosball, poker), basement arcade games, board games & outdoor games ✨ Four bedrooms, 5 king beds, and a 🛋 sofa sleeper in speakeasy (sleeps 12 total) 🐾 Pet Friendly ✨ 5 Minutes to grocery & Gas ✨ Stocked chef's kitchen ✨ 10 min to DT La Grange

Top guest favourite

Home in Prospect

5 out of 5 average rating, 9 reviews

NEW Bourbon Trail, Pet Friendly, Downtown, Shops

*Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required* Discover your ideal retreat at Watch Hill Norton Commons! Just steps from it all, this home gives you quick access to downtown Louisville, Bourbon Trail, horse farms, local dining, & entertainment. Enjoy community parks, pools, live music, & spots like the local YMCA with its gym & indoor pool. Near distilleries, horse farms, and golf courses. Book your Kentucky adventure today!

Top guest favourite

Home in Crestwood

5 out of 5 average rating, 57 reviews

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!

Guest favourite

Home in La Grange

4.93 out of 5 average rating, 14 reviews

Barn + House | 30 Acres | Pickleball | Basketball

This is the perfect spot for your group. Sleeps 14! 4 King beds 3 queen beds! Outdoor amenities: +30 acres with trails + 2 Pickleball Courts +Full court Basketball +Soccer Field +Playground +Springless Trampoline +Fire pit +Grill +Corn hole Game Barn features +Pool Table +Ping Pong Table +Poker Table +Arcade: Pinball, head to head, retro games +2 Smart TVs +Foosball +Loft area +Starlink internet House Amenities: +2 Living Rooms +Large Deck +2 Kitchens +Kid-friendly + 3 Full Bathrooms

Guest favourite

Home in La Grange

4.93 out of 5 average rating, 110 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.

Guest favourite

Home in Crestwood

4.9 out of 5 average rating, 103 reviews

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

Top guest favourite

Home in La Grange

4.97 out of 5 average rating, 95 reviews

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.