Pet-friendly vacation rentals in Oldham County

Cozy hideaway on Yankee creek.

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. The Hideaway is close to the Ohio river and there’s room to park a boat.

Peaceful home with river views

A secluded two story house on beautiful property by the river. The nearest neighbors are on the other side of the tree lines. The front Dutch door opens up to hardwood floors with instant views of the Ohio River. Fiber optic internet and Wi-Fi. Apple TV. Well-stocked kitchen (spices and appliances). No sirens or traffic noise. Guests reportedly love having morning coffee on the back porch overlooking the river. Respect the quiet vibe in this valley, no loud parties or music after 7:00 pm.

NEW Bourbon Trail, Norton, Pets Allowed, Downtown

Step into your fall retreat in the heart of Norton Commons! Watch Hill Manor is your gateway to exploring downtown Louisville, Bourbon Trail, and rolling horse country. Enjoy crisp autumn days with a stroll to downtown local shops, great local dining, and community events right outside your door. The location also provides easy access to bourbon distilleries, scenic horse farms, golf courses, and seasonal activities like festivals and foliage tours. Book your Kentucky getaway today!

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.

Historical Mansion 7BD Vacation Home in Derby City

Stay in a historic landmark listed on the National Register of Historic Places and recognized by the Kentucky Heritage Council. This fully updated home sits on 7 private acres with a pond, outdoor space, and a private entrance. Perfect for family getaways or group stays. Enjoy peace and privacy while being just minutes from dining, shopping, and local attractions. A rare blend of history, comfort, and convenience.

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!

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage 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. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

Cozy Cottage | Hot Tub + Holiday Ready

Book your holiday escape at Crestwood Cottage! Our cozy retreat features a decorated Christmas tree, festive touches, private hot tub, dedicated workspace, and a fenced backyard perfect for pets or enjoying crisp fall and winter air. Just minutes from Louisville and bourbon distilleries—ideal for holiday gatherings, family trips, or winter getaways.

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.