House holiday rentals in Shelbyville

Bourbon Central Waterfront Luxe near Buffalo Trace

This Ultra Luxe River Flat located in the heart of the Capital City of Frankfort, Ky offers 1600 square feet of step free luxurious, modern living within walking distance to everything downtown has to offer- 15+restaurants/pubs. 1.8 miles to Buffalo Trace, less than 10 miles to Woodford Reserve, Castle & Key and Whiskey Thief. -King Size Bed Suite -Heated floors in main bath -1 Gig Wifi -75" /55" Smart TVs/Direct TV/Apps - Coffee Station w/Decaf and tea - Piano, Guitar - Golden Tee Ms. Pac-Man

Location · Value · TV

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

Location · Family · Bathroom

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

Location · Family · Pool

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Location · Value · Hiking

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

Value · Family · Outdoor spaces

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Location · Value · Comfort

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Family · Location · Long stay

The Bourbon Sanctuary

NEWLY remodeled home on the Bourbon Trail! This home has 2 bedrooms & 2 baths with a king size bed in one room and a queen in the other. Close proximity to several distilleries and local wineries here in the bluegrass state! You will find a peaceful atmosphere along with some horse farms on your drive to the distilleries. This home is within a mile of Castle & Key distillery and Woodford Reserve! The sunsets are beautiful and you will most likely see wildlife right outside the back door!

Location · Family · Indoor spaces

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Location · Family · Getting around

Comfort in the Bluegrass

Comfort in the Bluegrass is a very clean, home nestled in the heart of bourbon and horse country. If it’s a little R&R you’re after, or entertainment…. This is the perfect location for either! We sit in a beautiful 1.6 acres located in a quiet, peaceful area in Anderson county. You can choose to relax with your friends or family by the fire pit, or tour one (or several) of the many sites around here! We are in between Lexington and Louisville, and only a few miles from Frankfort.

Family · Location · Cleanliness

Lakefront Horse Farm | Sleeps 12 | Bourbon Trail

Experience Kentucky horse country from your own private lakefront retreat. Nestled on a working Thoroughbred farm and sleeping up to 12 guests, this spacious home is perfect for Bourbon Trail weekends, family gatherings, golf trips, and peaceful escapes in the Bluegrass. Conveniently located between Louisville, Lexington, and Frankfort. Relax on the porch bed swing, gather around the fire pit, or enjoy air hockey, foosball, cornhole, bucket golf, and a basketball shootout.

Value · Location · Access

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, peaceful home, thoughtfully designed with comfort and style in mind. This cozy haven offers a relaxing place to unwind after a day of exploring bourbon country. Just minutes from Castle and Key and Woodford Reserve and only ½ mile from the highly rated restaurant and bourbon bar, The Stave. Whether you’re here for tastings, scenic drives, or quiet evenings in, Limestone Landing puts you right where you want to be!

Location · Family · Check-in