Holiday rentals in Oldham County

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!

4.86 out of 5 average rating, 189 reviews

Guest suite in Prospect

Private Entry, full suite w/game rm. Kitchenette.

Golf course community, walkout basement with private entry. Flat screen TV, WiFi, Private Bedroom. Large Family rm with pull out Queen sleeper sofa, pool table, Hardwood floors. Refrigerator, microwave and coffee maker, Keurig. Toaster/hot plate and basic dishes/ cooking utensils are included. (one review stated dishes weren't clean) I was trying the whole open shelf look and didn't realize I would need to clean the dishes more often since they weren't in a cabinet) Private patio. Large yard.

5 out of 5 average rating, 108 reviews

Home in Prospect

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!

4.98 out of 5 average rating, 119 reviews

Cottage in Prospect

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.

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

4.98 out of 5 average rating, 221 reviews

Tiny home in La Grange

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

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.

4.9 out of 5 average rating, 104 reviews

Home in Crestwood

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

4.97 out of 5 average rating, 225 reviews

Guest suite in Prospect

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.

4.98 out of 5 average rating, 170 reviews

Cabin in La Grange

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.

4.99 out of 5 average rating, 139 reviews

Farm stay in Pendleton

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 65 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.

4.98 out of 5 average rating, 333 reviews

Farm stay in Goshen

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....

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oldham County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oldham County

Campervan/Motorhome in Crestwood

5 out of 5 average rating, 14 reviews

Airstream Farm Stay Getaway!

MindyRating, 5 stars2 weeks ago

Beautifully redone Airstream! Comfy beds, great AC, cute outdoor sitting area, friendly farm animals & perfect barn to over night our horses! We enjoyed our stay and would certainly stay again when in town for a horse show! I would note there are regular trains throughout the night approx 75 yards away. Overall, great communication & welcoming from Jessica in a beautiful setting.

4.81 out of 5 average rating, 16 reviews

Home in Prospect

Secluded cottage on farm.

KyleRating, 5 stars1 month ago

What a wonderful farm cottage! Anna was very helpful getting us set up in a relaxing, peaceful place. After our first night, she checked in to make sure everything was going well and suggested activities we could do. Would highly recommend

4.98 out of 5 average rating, 49 reviews

Home in Crestwood

2King beds+HotTub+FirePit

LorrieRating, 5 stars3 weeks ago

We wanted a quick, midweek, night away for our 20th Anniversary. We’d had a particularly overwhelming a stressful, busy couple of weeks with other family commitments and a death near the family. We booked the day before our stay- very last minute! Becky & Heather were fantastic hosts. The house was ready, the hot tub looked brand new it was so clean, the backyard is an oasis of relaxation, and everything was just perfect. We were able to relax and enjoy! We ordered take out from the nearby Crestwood Bistro- delicious!! Just wish we’d had more time. We’ll definitely recommend Becky & Heather’s place to friends and family.

4.97 out of 5 average rating, 86 reviews

Cabin in Goshen

Little piece of heaven in Kentucky horse country.

TimRating, 5 stars1 month ago

Dominique’s cabin is amazing! Peaceful surroundings. We booked for the Kentucky Derby and could not have been more happy with the place. Only wish I could have spent more time there. Will definitely try to make it back up in the winter to use the fireplace. She is the most gracious host I’ve ever had. Even had fresh flowers waiting on the table for us. Couldn’t have asked for a better host!

5 out of 5 average rating, 16 reviews

Home in Prospect

CIRCO LOCO - uNCommon Stay

KatieRating, 5 stars6 days ago

We had an amazing stay! The listing was even better than the photos presented… the decor was fabulous, the furnishings were such high quality, and the listing had everything we needed for our stay. Our hosts were very responsive and answered any questions so quickly. The neighborhood has great restaurants, cute little shops, and three different swimming pools to choose from… all walkable! My children said it was “better than the beach”! They even have a common work space in the floor below the unit, which was great for when I needed to work and have some quiet. Definitely 10/10 recommend!

4.93 out of 5 average rating, 61 reviews

Loft in Charlestown

Cozy hideaway on Yankee creek.

ToddRating, 5 stars3 months ago

Nice place to stay in the woods. We were able to have our dog with us. Very quiet, but yet still close to ammenities.

5 out of 5 average rating, 68 reviews

Home in Goshen

Relaxing River Retreat with Private Pool

MaryRating, 5 stars8 months ago

Absolutely perfect! I would say this AirBnb is one of the best that we’ve stayed at. Amazing views of the river. Kristen was very responsive and had everything we needed at the house. The kitchen was stocked with everything you need to cook meals. Beds were comfortable and there were plenty of towels and hot water! I definitely recommend Kristen’s house! I know I didn’t want to leave!