Holiday rentals in Shelbyville

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Top-rated holiday rentals in Shelbyville

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 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!

30 Aug – 6 Sept

£132 per night
Guest favourite

Chalet in Lawrenceburg

4.96 out of 5 average rating, 142 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!

26 Mar – 2 Apr

£124 per night
Superhost

Home in Shelbyville

4.81 out of 5 average rating, 112 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

28 Jul – 4 Aug

£165 per night

Popular amenities for Shelbyville holiday rentals

Stay near Shelbyville's top sights

Walmart Supercenter4 locals recommend
Claudia Sanders Dinner House16 locals recommend
Cracker Barrel Old Country Store5 locals recommend
Jeptha Creed Distillery36 locals recommend
La Cocina de Mama12 locals recommend
Milano Italian Restaurant3 locals recommend

Other great holiday rentals in Shelbyville

Guest favourite

Farm stay in Shelbyville

5.0 out of 5 average rating, 30 reviews

Cozy Apartment at Red Gate Farm

19–26 Oct

£88 per night
Guest favourite

Guest suite in Shelbyville

5.0 out of 5 average rating, 60 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

1–8 Sept

£109 per night
Guest favourite

Flat in Shelbyville

5.0 out of 5 average rating, 44 reviews

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

8–15 Jul

£117 per night
Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 33 reviews

Spacious suite, country views, pool table, firepit

13–20 Mar

£112 per night
Guest favourite

Farm stay in Shelbyville

5.0 out of 5 average rating, 15 reviews

Bourbon trail apartment on horse farm

7–14 Jan

£87 per night
Guest favourite

Guest house in Shelbyville

4.96 out of 5 average rating, 70 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

29 Aug – 5 Sept

£140 per night
Guest favourite

Guest suite in Louisville

4.96 out of 5 average rating, 28 reviews

Middletown Private Guest House

29 May – 5 Jun

£87 per night
Guest favourite

Cabin in Lawrenceburg

4.96 out of 5 average rating, 25 reviews

Hidden View Cabin

21–28 Feb

£104 per night
Guest favourite

Home in Shelbyville

4.84 out of 5 average rating, 38 reviews

Bourbon Basecamp! New on the Bourbon Trail!

18–25 Feb

£182 per night
Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 8 reviews

Pool*HOT TUB*Bourbon Trail

28 Oct – 4 Nov

£329 per night
Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 15 reviews

oasis 522

23–30 Dec

£160 per night
Guest favourite

Home in Simpsonville

4.94 out of 5 average rating, 63 reviews

Comfortable sleek home bourbon trail

16–23 Jun

£151 per night

Quick stats about holiday rentals in Shelbyville

Total rentals

40 properties

Wifi availability

40 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1.5K reviews

Nightly prices starting at

£24 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Shelby County
  5. Shelbyville