Holiday rentals with a patio in Shelbyville

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Top-rated rentals with patio in Shelbyville

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Guest favourite

Train in Lawrenceburg

4.99 out of 5 average rating, 268 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm 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 bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

14–21 Jan

$259 SGD per night

Guest favourite

Cottage in Wilmore

4.98 out of 5 average rating, 164 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

25 Sep – 2 Oct

$170 SGD per night

Guest favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 155 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

11–18 Mar

$203 SGD per night

Guest favourite

Home in Jeffersonville

4.95 out of 5 average rating, 153 reviews

Cheerful 2 bedroom home, close to downtown

2 bedroom home & 1.5 bath. Fenced private courtyard. Walk to parks, dining & shopping in downtown Jeffersonville. Across the bridge from Louisville! Lots of light, chef's kitchen w kitchen wares and expandable dining table. 2 bedrooms (queen beds), and a comfy couch. Street parking w designated spot. We live on the street & use a security camera to confirm your arrival, departure, # of reserved guests. Non Smoking home. 8 min drive: Yum!Center/Convention Center/Bourbon distilleries/ restaurants

31 Jul – 7 Aug

$128 SGD per night

Guest favourite

Home in Shelbyville

4.85 out of 5 average rating, 40 reviews

Bourbon Basecamp! New on the Bourbon Trail!

You made it to Bourbon Basecamp in Shelbyville, KY! We are in the heart of bourbon country which gives you an opportunity to experience the best of what the bourbon trail has to offer! Being only 20 min west of Frankfurt, 20 min east of Louisville, and 40 min west of Lexington, our basecamp is perfect for daily expeditions! And come explore Shelbyville, the Saddlebred capital of the world! There are plenty of local events and attractions to experience the amazing equestrian culture here in KY!

3–10 Nov

$286 SGD per night

Guest favourite

Home in Frankfort

4.99 out of 5 average rating, 104 reviews

The Julep - Cozy yet spacious, near local hotspots

Families or groups will love the open & welcoming floor plan that makes it easy for all to spend time together OR a quiet moment alone. Restaurants, shopping, Bourbon tours, family entertainment, canoe, river & nature trails are only a short drive away. Situated between Lexington & Louisville, "The Julep" allows you to explore Kentucky while staying in the charm of the Capital City. Newly renovated 5BR/3BA, "The Julep" is ideal for a short or long term stay, whether it's for work or play.

20–27 Feb

$584 SGD per night

Guest favourite

Farm stay in Lancaster

5.0 out of 5 average rating, 143 reviews

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

14–21 Feb

$279 SGD per night

Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 35 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

27 Nov – 4 Dec

$181 SGD per night

Guest favourite

Treehouse in Georgetown

4.94 out of 5 average rating, 170 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

4–11 Jul

$263 SGD per night

Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 34 reviews

Bluebird Cottage- A New Spot on the Bourbon Trail!

Original Charm with a modern twist - and larger than it looks! Freshly updated 1900's shotgun house in a quiet neighborhood. Convenient to the great things central Kentucky has to offer. You can travel east to Bulleit Bourbon Experience in 15 minutes, or west to enjoy all the action of Downtown Louisville in about half an hour. Wonderful local restaurants nearby. Shelbyville is the Saddlebred Horse capital of the world and is part of the famed Bourbon Trail.

12–19 Sep

$395 SGD per night

Guest favourite

Home in Frankfort

5.0 out of 5 average rating, 125 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.

3–10 Feb

$335 SGD per night

Guest favourite

Home in Frankfort

4.97 out of 5 average rating, 165 reviews

Bourbon Trail Hideaway on the Kentucky River!

Escape to a private retreat on the Kentucky River. This home offers 2 private bedrooms and a large loft area. Enjoy your coffee on deck over looking the river. 5 miles to Buffalo Trace Distillery. 3 miles to Kentucky Capital. 7 miles to Castle & Key Distillery. 12 miles to Woodford Reserve Distillery 14 miles to Wild Turkey Distillery. 17 miles to Four Roses Distillery. Grill, coffee pot included.

14–21 Feb

$325 SGD per night