
Family-friendly holiday rentals in Shelbyville
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shelbyville
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Mini Cow Cottage! Peaceful Farm Getaway
Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland and High Park cattle, a horse, friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

Hide away close to everything
Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Comfortable Charm on the Bourbon Trail
You’ll be charmed by this adorable place to stay, close to the interstate, making travel to Valhalla Golf Course, bourbon distilleries, Churchill Downs, and other attractions in nearby Louisville a breeze. We are in a beautiful rural setting, just right for relaxing. Our space has its own private entrance with a comfortable living room and private bathroom downstairs, and features a loft with queen bed and desk. There are a microwave, coffee maker, and fridge available for your convenience.

Historic Cabin by Bourbon Trail
Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Bourbon Trail: Caboose on the Farm
Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Sweet Hollow Farm
Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

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

Tiny House Farm Stay on One Goat Farm
This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery. Located in the heart of an Amish community. We breed, show and raise registered myotonic goats. We have a fall and spring kidding season so if you book during that time, expect to see baby goats frolicking in the fields. The cottage is on a functioning farm with horses, cats, goats and a donkey. We offer overnight housing facilities for your own equines as well.

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.

Treetop Hideaway
Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Tiny Home with Huge Charm near the Elkhorn Creek
Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!

Olive Branch Suite with projector screen in E Lou
This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.
Popular amenities for Shelbyville family-friendly rentals
Family-friendly home rentals with a hot tub

Cherokee Park Oasis with Private Entrance

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

4th Street Suites - Comfortable King Bed Suite

Glow Hill - Hot Tub! Ark 30 min - Horse Prk 13 min

Walking Bridge, Putt Putt House

The Luxe/HotTub/Playground/12min KHP/30min Ark

Bourbon Trail Bliss by the Lake, HotTub, Kayaks

Bourbon Trail*Pewee Valley *HOT TUB
Family- and pet-friendly home rentals

Private Prospect Flat

Highlands Lower Level Studio Guest Suite

Quiet Neighborhood Home With Outstanding Location

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

River House - Cottage with KY River View & Access

*Unique Country Cabin *1BR 20 min from The Ark!

Eco+ guest suite in the center of all the fun

Countryside On the Bourbon Trail, 22 Quiet Acres
Family-friendly home rentals with a pool

The Bunkhouse at Big Red Stables

Cozy studio with private pool and firepit

Peaceful Cottage Minutes from Lake Access

Peppermint Cottage Norton Commons w Breakfast

Luxury Retreat with Hot Tub

Cottage on the Bourbon Trail

The Gathering Place

Come Explore Jeffersonville & Louisville
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $342 NZD | $397 NZD | $381 NZD | $411 NZD | $474 NZD | $420 NZD | $442 NZD | $440 NZD | $442 NZD | $411 NZD | $324 NZD | $324 NZD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 7°C | 3°C |
Quick stats about holiday rentals that are family-friendly in Shelbyville

Total holiday rentals
Explore 30 holiday rentals in Shelbyville

Nightly prices starting at
Shelbyville holiday rentals start at $72 NZD per night before taxes and fees

Verified guest reviews
Over 1,740 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Shelbyville holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Shelbyville rentals

4.9 Average rating
Shelbyville stays are highly rated by guests—averaging 4.9 out of 5!
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- Ark Encounter
- Kentucky Horse Park
- Buffalo Trace Distillery
- Rupp Arena
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Valhalla Golf Club
- Angel's Envy Distillery
- Muhammad Ali Center
- Heritage Hill Golf Club
- Charlestown State Park
- Louisville Slugger Field
- Anderson Dean Community Park
- Louisville Slugger Museum & Factory
- Turtle Run Winery
- Falls of the Ohio State Park
- Kentucky Science Center
- Big Four Bridge
- Waterfront Park
- Old Fort Harrod State Park
- Hurstbourne Country Club
- River Run Family Water Park
- Talon Winery & Vineyards
- Big Spring Country Club




