Pet-friendly holiday rentals 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.

The Ultimate River House! Derby Week Discount!

Forget your worries and relax with your family in this newly updated 4BR/3BA home with stunning river views and a private dock for fishing, swimming and paddle-boarding. Enjoy the sprawling 3-tier deck with incredible river views and plenty of seating for the entire family. The patio also features a gas grill and fire pit. The interior is designed for comfort and relaxation, with cozy living areas, a well-equipped, chef's eat-in kitchen, a large, formal dining room, amazing master suite/balcony

SuperHost ~ Quiet Upscale Home Near Louisville

🏡 Peaceful Neighborhood Enjoy a calm, residential setting with easy access to everything Louisville has to offer. 🌳 Close to Parks & Scenic Drives Surrounded by green space and beautiful Kentucky landscapes—perfect for relaxing stays. 🛍 Minutes to Shopping & Dining Quick drive to Paddock Shops, Norton Commons, and East End favorites. 🚗 Easy Access to I-265 & I-71 Convenient routes to downtown Louisville, Churchill Downs, and the airport. 🛏 Book now and unwind in a serene Kentucky home!

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

Loft 2bedroom/1bath in PeweeValley near Louisville

Welcome to our charming Pewee Valley loft! This tastefully decorated 2-bedroom, 1 bathroom space is an inviting retreat for your next getaway. Nestled in a peaceful town, it offers a perfect blend of comfort and serenity. Lounge in the cozy living area or enjoy a cup of coffee on the private balcony. Conveniently located near local attractions and with easy access to nearby cities, this hidden gem is ready to make your stay unforgettable. Book now and experience the charm firsthand!

Cozy Hideaway

You will love The Cozy Hideaway! A great place to rest and relax, also enjoy this great central location to explore Southern Indiana! Only 20 minutes to Jeffersonville & 20 minutes to the Lewis and Clark bridge to Louisville. Situated in between Charlestown and New Washington. Very near beautiful hiking at Charlestown State Park or head up the Ohio river scenic by-way to Clifty Falls State Park in Madison, Indiana. We are dog friendly , only one dog and a pet fee required.

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

...Happy Trails House in Derby City

4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher

Riverfront Cottage

Wake up to peaceful Ohio River views at this charming 2-bed, 1 bath waterfront cottage, where mornings start with coffee on the screened porch and evenings end watching the sunset over the water. With private dock access, cozy indoor spaces, and a quiet setting just 25 minutes from downtown Louisville, this home is perfect for couples, small families, or anyone looking to unplug and relax by the river.

Bourbon Trail*Tesla EV charging* 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!

Welcome to the Nest!

Welcome to THE NEST! We are located very close to great local restaurants, the best outdoor bar/venue I've seen (Third Turn - Oldham Gardens), Artisan Distillery (home of Jefferson's Ocean Bourbon), all major amenity needs, and beautiful Kentucky backroads; all while being easy to access from major highways. Your private retreat is sure to please.

Crestwood Louisville | Hot Tub | Bourbon Trail

Welcome to Crestwood Cottage — a warm, inviting home in Crestwood, a charming suburb of Louisville, designed for rest, connection, and comfort. Enjoy a private hot tub, cozy living spaces, and a location that makes exploring Louisville and planning bourbon trail day trips easy and enjoyable.