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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Guest favorite

Home in Lawrenceburg

5.0 out of 5 average rating, 64 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.

Oct 28 – Nov 4

R2,868 ZAR per night

Guest favorite

Chalet in Lawrenceburg

4.96 out of 5 average rating, 148 reviews

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!

Dec 1 – 8

R2,566 ZAR per night

Guest favorite

Farm stay in Simpsonville

4.86 out of 5 average rating, 63 reviews

Farm House - near Bourbon Trail & Pet Friendly

Late 1800's farm house on a 155 acre working family farm located in the heart of the Bourbon Trail. It is a unique experience to stay on our farm where we raise non-GMO corn that goes into producing bourbons here in Kentucky. The farm is rural and private, but convenient to Louisville, distilleries and many other local attractions. We are located only 10 minutes from the Gene Snyder Freeway in Louisville and 10 minutes from the Outlet Shops of the Bluegrass and 15 minutes from Shelbyville.

Jun 9 – 16

R2,636 ZAR per night

Superhost

Home in Shelbyville

4.8 out of 5 average rating, 117 reviews

Parris on Main

Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville and, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite to eat. **Update - brand new ac system installed 7/19/2023 Newly renovated, built in 1942, this house is perfect for a family or group of friends wanting to experience the wonderful places Kentucky has to offer. Right in the middle the Bourbon Trail and about 30 minutes from ChurchIll Downs

Nov 6 – 13

R3,528 ZAR per night

Guest favorite

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.

Oct 22 – 29

R2,450 ZAR per night

Guest favorite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 72 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. You may even see our free range chickens on your way. Take in nature, as you’re surrounded by trees and a creek that flows down from the deck - all while 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.

Jul 11 – 18

R2,718 ZAR per night

Guest favorite

Home in Pleasureville

5.0 out of 5 average rating, 82 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.

Mar 31 – Apr 7

R2,652 ZAR per night

Guest favorite

Guest suite in Crestwood

4.95 out of 5 average rating, 63 reviews

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

Jul 22 – 29

R2,107 ZAR per night

Guest favorite

Farm stay in Shelbyville

5.0 out of 5 average rating, 16 reviews

Bourbon trail apartment on horse farm

Don't just visit Kentucky, experience it! Join us at Celebration Acres in beautiful Shelbyville. Centrally located between Louisville & Lexington, this private unit is your refuge as you explore bourbon country. We're 5 min from Bulleit, & under 20 miles to Jeptha Creed & Buffalo Trace. Here for the horses? We're close to Kentucky Horse Park & Churchill Downs. Our horses & donkeys are on property & available for a meet & greet for a unique memory & photo opportunity.

Mar 6 – 13

R1,852 ZAR per night

Guest favorite

Cabin in Shelbyville

4.92 out of 5 average rating, 52 reviews

Arcade | Fishing Pond | Cabin on Farm | Slps 12+

Last Minute Availability Alert! The Rec Farm: Your Ultimate Derby Destination! This stunning retreat, although not new to the Bluegrass Stays Collection, has just opened up for last-second bookings. Situated a mere 10 minutes from I-64, it offers unparalleled convenience for those seeking easy access to the Churchill Downs excitement. Sleeps 13 along with amenities like an arcade, hot tub, and fire pit. Secure your spot now and make your Derby dreams a reality!

Aug 1 – 8

R17,366 ZAR per night

Guest favorite

Condo in Shelbyville

4.93 out of 5 average rating, 123 reviews

Horses, Bourbon, and More .... Shelbyville Condo

Beautiful condo duplex features 2 bedrooms / 2 full bathrooms, light open floor plan, private entrance with parking at the door.. Close to shopping, expressway, local wineries, bourbon distilleries, horse farms and much more!! Fully Furnished including linens, towels, dishes and more! Work or travel, we welcome you to your home away from home! Located Close to shopping, farms, local interests and I64.. 25 minutes to Louisville, 45 minutes to Lexington.

Sep 18 – 25

R2,096 ZAR per night

Guest favorite

Home in Shelbyville

4.96 out of 5 average rating, 55 reviews

Bass N Bourbon Retreat - Lakefront * Bourbon Trail

House on Guist Creek Lake near Bulleit Distilling Co. 3 bedroom/2 bath house has all the benefits of enjoying the lake, traveling KY’s Bourbon Trail, & relaxing at a peaceful getaway. Three furnished bedrooms: king, queen, and two twin beds with an optional queen sofa bed in the front living room. Kitchen is fully furnished. Den offers a beautiful picture window for you to enjoy lake view. Patio w/table & chairs on a lighted porch. Seasonal: 2 Kayaks

Sep 26 – Oct 3

R6,133 ZAR per night