Vacation rentals with outdoor seating in Shelby County

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Top-rated outdoor seating rentals in Shelby County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Lawrenceburg

4.97 out of 5 average rating, 152 reviews

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.

Guest favorite

Home in Shelbyville

5 out of 5 average rating, 23 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

A great centrally located 4 BR 2.5 Bath (6 beds) dog-friendly house near downtown Shelbyville! Located in a cul-de-sac on a quiet street in a family friendly neighborhood 6 miles from Bulleit Bourbon, 3 miles to Jeptha Creed Distillery, and 1 mile from the Shelbyville Horse Show. Fully updated & stocked, coffee pot (K-cups or ground), washer/dryer, & 5 smart TVs. This rental has everything you need and proximity to Churchill Downs, multiple Bourbon Trail distilleries, Louisville, and Frankfort!

Guest favorite

Home in Finchville

4.92 out of 5 average rating, 118 reviews

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.

Guest favorite

Guest suite in Shelbyville

4.94 out of 5 average rating, 18 reviews

Country guest suite. Bourbon trail close by.

Welcome to Kentucky! We have the perfect newly renovated guest suite for visitors whether you are headed to our famous Kentucky Derby, Bourbon Trail tours, or more. You will have your private entrance, a comfortable living area, a fully stocked kitchenette, a full bath, one bedroom with a queen bed, and a living room with a large sectional couch and TV. WiFi is available, and we are a short drive to Frankfort, Louisville, and Bardstown. #distillerytours#bourbon #bourbontrail #derby#railfest

Guest favorite

Chalet in Lawrenceburg

4.96 out of 5 average rating, 211 reviews

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! 22 acres of privacy. Cows may be present in pasture. 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 we look forward to sharing it with you. Hosted by the owners.

Superhost

Cabin in Shelbyville

4.93 out of 5 average rating, 101 reviews

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

Top guest favorite

Home in Shelbyville

5 out of 5 average rating, 15 reviews

WelcomeTreatsWaiting| CentralLocation| Comfortable

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

Top guest favorite

Home in Pleasureville

4.99 out of 5 average rating, 101 reviews

Pleasureville - The name says it ALL

This location is a Pleasure! Cozy Kentucky home off the beaten path, but close to attractions. Imagine after a full day on the bourbon trail enjoying your own piece of Kentucky with a drink in your hand. Access to 25+ acres of beautiful farmland and super clean, fully stocked private home. Close to the Outlet Shoppes of the Bluegrass making it a perfect ladies weekend get away. Additional meeting/event space available in the renovated on site barn. Reminder No Pets allowed.

Top guest favorite

Guesthouse in Shelbyville

4.97 out of 5 average rating, 117 reviews

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.

Top guest favorite

Cabin in Lawrenceburg

4.99 out of 5 average rating, 93 reviews

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

Top guest favorite

Condo in Shelbyville

4.94 out of 5 average rating, 143 reviews

Work, Play or Bourbon $99 nights thru 8/31

2-bedroom, 2 full bathroom condo offers a one level floor plan and a private entrance with parking at your door. Just a few minutes to Bulleit Distillery, you will be located in the center of the Bourbon Trail. Here for work? Grocery, shopping, interstate are within a few minutes. In town for a festival? Let us help you plan with local recommendations and hidden gems! All the essentials are provided and a few extra special touches too.

Top guest favorite

Home in Shelbyville

5 out of 5 average rating, 37 reviews

The Back 40 ~ Modern*Scenic*Private*EV Charging

The Back 40...where rural charm meets the modern amenities you expect. Overlooking the Jeptha Creek and situated in a serene Kentucky cattle pasture, this piece of country gold is your gateway to Kentucky's lauded Bourbon Trail and the Saddlebred Capital of the World. The Back 40 is perfect for Bourbon Trail adventurers, those seeking a little retail therapy, or folks simply aiming to escape to a slower pace of life for just a spell.