Holiday rentals with outdoor seating in Shelby County

Cozy Studio Loft Cabin in the Woods Louisville, KY

Experience the Best of Both Worlds: Extreme Country Living within Louisville City Limits. Just a stone's throw from the city's hustle and bustle, yet surrounded by the tranquility of nature, this is the perfect home for anyone looking to have it all. Just 3 miles from Kroger grocery, bank, restaurants and a liquor store. Just 20 minutes from Downtown, Mohammad Ali Airport (SDF), Fairgrounds, Valhalla Golf Course, the infamous Bourbon Trails and many other famous sites in the Louisville area.

Thoroughbred Horse Farm Cabin-located on Lamb Lake

Beautiful cabin located on a working horse farm just miles from Louisville, Frankfort and Lexington! Take in the farm scenery from our porch bed swing, or large patio with fire pit. Play a round of Air hockey, foosball, basketball shootout, corn hole, or bucket golf during your stay! Several Bourbon Distilleries are within a 30 minute drive of the property. The Cabin is 4 miles from the Outlet Shoppes of the Bluegrass, 15 miles from Taylorsville Lake, and 13 miles from Valhalla Golf Course.

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! Full access to 22 acres with beautiful hilltop sunsets. In the heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and it will soon be in your dreams as well. Hosted by the owner!

WillHelpFloodVictims | DerbyDiscount | WelcomeTreat

Cozy 750 sqft home designed for convenience and comfort 1 bdrm w/ comfy queen bed, 1 bath and a pull out couch Stocked w/ snacks, toiletries, and coffee & tea options Outside enjoy the fire pit (wood provided) or fire up the grill for a burgers or steak Located across from the fairgrounds in safe, charming downtown Shelbyville, you'll have easy access to local events, dining, and shopping Whether you're here to explore the Bourbon Trail or just unwind this spot offers everything

Bourbon by the Lake

Peaceful, Beautiful 4 bedroom, 2 bathroom house sitting on Guist Creek Lake in Shelbyville, KY located very close to the Bulleit Bourbon Distillery. Lake view from two of the four bedrooms. Perfect for bird watching. Guist Creek Lake is a great kayaking and fishing lake. Patio off the main living room with patio table and chairs. Two comfortable living room spaces with smart TVs, games, and books. Beautiful sunroom overlooking the lake. Nice patio space. Lake access with boat dock.

Airstream Farm Stay Getaway!

Enjoy some time away on a farm in a customized remodeled 1977 Airstream Sovereign! Top of the line details inside - a warm and cozy farm outside! Spend time with the horses, pigs, chickens and cats during your visit! Whether it is picking flowers in the garden or starting a fire in the solo stove! We have everything you need to reconnect to nature in Luxury! PLEASE TAKE NOTE! The toilet is a composting toilet. Special instruction for use in manual. EASY AND CLEAN TO USE.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

NEW - Hot Tub, Fully Loaded, 10 min to Bulleit

Escape to our serene haven nestled in the heart of the Kentucky Bourbon Trail. This inviting property offers the perfect home base for your bourbon tasting adventures. The Bourbon Bungalow is located in a rural/residential area across the street from Guist Creek Lake in the charming town of Shelbyville. We are midway between Louisville and Lexington and perfectly situated for visits to a plethora of distilleries.

Urban Loft Sleeps 16 and close to Buffalo Trace

"The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably cohabitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave." - Bourbon Review Magazine