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Shelbyville Holiday Rentals

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Holiday Rentals in Shelbyville

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

9.8 out of 10, Exceptional, (12)
"Very convenient to Louisville, Frankfort and Lexington. "
The price is AU$688
includes taxes & fees
28 July - 29 July
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION

10.0 out of 10, Exceptional, (70)
"Awesome place!! The loft was unique, homey, and beautiful. Hosts were great. "
Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

10.0 out of 10, Exceptional, (27)
"The pictures are an accurate description of the property. The hosts were very easy to communicate and ask questions.It was VERY clean and comfortable. We had 6 adults and a toddler. The houses across the street were a little sketchy, but we'd definitely book again or refer someone to that house!"
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!

10.0 out of 10, Exceptional, (15)
"The cabin and area was very beautiful. I would certainly rent this cabin again. Host was easy to work with, cabin very clean, and kitchen stocked with nice dishes & pans."
Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!

Shelbyville Home - On to the Bourbon Trail!

7.4 out of 10, Good, (13)
"We absolutely loved staying here. I brought a group up to go to a conference in Louisville Kentucky. The amenities were very nice. Everything was clean and organized. And it’s a gorgeous area."
Shelbyville Home - On to the Bourbon Trail!

Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail

9.8 out of 10, Exceptional, (43)
"Home was clean and in good shape. We had 4 adults and 1 child and had plenty of room. We loved the private dock for fishing and the fire pit for s’mores. The beautiful view from the living room was a highlight of the house! "
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

9.8 out of 10, Exceptional, (70)
"This place was a perfect stay for my bachelor party! There was a ton of room, the host was very responsive with any questions and it had everything we needed. Highly recommend! "
The price is AU$1,759
includes taxes & fees
10 Aug - 11 Aug
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cozy Tree-Lined Carriage Home - Stay in Serenity!

9.4 out of 10, Exceptional, (9)
"We absolutely loved staying here while in town visiting family. This place is spacious and beautifully decorated with lots of amenities. We would definitely stay here again. "
The price is AU$255
includes taxes & fees
28 July - 29 July
Cozy Tree-Lined Carriage Home - Stay in Serenity!

Capital City Cottage

9.2 out of 10, Wonderful, (32)
"We were very pleased with he place. The beds were very comfortable and the amenities well thought out and nice."
The price is AU$370
includes taxes & fees
3 Aug - 4 Aug
Capital City Cottage

Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

10.0 out of 10, Exceptional, (216)
"We enjoyed the stay"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

8.4 out of 10, Very good, (32)
"Great location, nice little unit! Parking is a bit tight! Would stay again!"
The price is AU$267
includes taxes & fees
18 Aug - 19 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

10.0 out of 10, Exceptional, (1)
"Our family of 8 adults and two young grandchildren absolutely loved this property! The home is beautifully decorated, and the kitchen is both stunning and fully equipped with everything you could possibly need, and more.The barn was a fantastic bonus: a fun and safe place for our grandsons to burn off energy before bedtime, and a perfect spot for the adults to unwind and enjoy games together.From the moment we booked until checkout, Melissa was incredibly responsive and helpful. We couldn’t have...
The price is AU$979
includes taxes & fees
28 July - 29 July
NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

8.8 out of 10, Excellent, (55)
"The property was nice and felt cozy the entire stay"
The price is AU$244
includes taxes & fees
28 July - 29 July
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

7500SqFt~Sleeps18~Themed Spaces~Bourbon Trial~Creek~Hot Tub~Sauna~Luxe Amenties

9.4 out of 10, Exceptional, (3)
"Very enjoyable!"
7500SqFt~Sleeps18~Themed Spaces~Bourbon Trial~Creek~Hot Tub~Sauna~Luxe Amenties

Cozy cabin w/ pool & hot tub! Close to Taylorsville Lake Marina & Bourbon Trails

9.4 out of 10, Exceptional, (47)
"Lovely quiet spot. We enjoyed our time here."
Cozy cabin w/ pool & hot tub! Close to Taylorsville Lake Marina & Bourbon Trails

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

9.8 out of 10, Exceptional, (7)
"Could not have asked for a better vacation rental than what we experienced at this lovely home in Frankfort, KY.The location between Louisville and Lexington made travel easy, access to the Bourbon trail was extremely convenient, and only about a 30 minute drive to the Keeneland Race Track.The house was exactly as advertised.... the garage has been converted to an amzing gameroom (golf sim, tv's, pool, air hockey, etc).... and the downstairs area of the home with a full bar, yoga, gym, theater,...
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

Modern cottage located in the heart of the Bourbon Trail

9.8 out of 10, Exceptional, (23)
"Very clean and great condition. Would stay again for sure. "
The price is AU$299
includes taxes & fees
30 July - 31 July
Modern cottage located in the heart of the Bourbon Trail

Spectacular waterfront house!

9.6 out of 10, Exceptional, (76)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

8.8 out of 10, Excellent, (92)
"Property is a great value in a good location to explore Frankfort "
The price is AU$254
includes taxes & fees
16 Aug - 17 Aug
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelbyville Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Shelbyville?

Yes, there are holiday rentals in Shelbyville close to Gallrein Farms, or you can select a more secluded option if you're looking for a relaxing stay. The shops and entertainment venues are just a few reasons why travellers like Shelbyville. Make sure you have time to check out the golf courses and cafés during your trip.

What are some of the best holiday rentals that Shelbyville has to offer?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: This holiday home rental outside of Shelbyville is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Shelbyville?

Choose from 29 Expedia holiday rentals in Shelbyville for a memorable holiday.

What can I see and do in Shelbyville?

Enjoy the area's cultural attractions such as Shelby County Community Theatre, or get outdoors into nature at a spot like Taylorsville Lake State Park. While here, Jeptha Creed Distillery and Guist Creek Lake State Park are other places worth a visit.

What are holiday rentals like in Shelbyville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelbyville. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for small groups.