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Shelbyville Vacation Rentals

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Jul 24 - Jul 25
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Jul 25 - Jul 27
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Aug 1 - Aug 3

Vacation Rentals in Shelbyville

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Relax in a serene space with a central hot tub, cushioned seating areas, and a ceiling fan.

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

10.0 out of 10, Exceptional, (26)
"The location is perfect for horse races and distillery tours. With it being located in between Lexington and Louisville, it was perfect for day trips to places of interest. "
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
4 bedrooms, free WiFi, bed sheets

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 ￥26,764
￥66,301 total
includes taxes & fees
Jul 28 - Jul 29
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
Relax in this stylish living room with a fireplace, exposed brick walls, and a large arched window.

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
Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!
Relax in this inviting room with a high ceiling, flat-screen TV, and bench with storage.

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!
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail
Relax in this inviting living room with a view of a serene tree-lined area, featuring two comfortable chairs, a TV, and a stylish rug.

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

9.8 out of 10, Exceptional, (43)
"We came to tour distillery’s "
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Enjoy cooking in this well-appointed kitchen with a stainless steel sink, wooden countertop, and range hood.

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 ￥92,132
￥180,201 total
includes taxes & fees
Jul 27 - Jul 28
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Enjoy a serene stay in a spacious two-story home with a deck and large windows.

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 ￥10,610
￥24,212 total
includes taxes & fees
Jul 28 - Jul 29
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Capital City Cottage
Cozy home with a gabled roof and a welcoming front porch.

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 ￥14,645
￥35,669 total
includes taxes & fees
Aug 3 - Aug 4
Capital City Cottage
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Relax in a hot tub with a clear view of the water's surface.

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
Kitchen features a large island with a granite countertop, double oven, and microwave.

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.
Relax on the deck with a bench and chairs, taking in the serene views of the lush landscape and cityscape.

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 ￥10,984
￥25,414 total
includes taxes & fees
Aug 17 - Aug 18
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
Enjoy meals in this dining area with a table set for a meal, surrounded by a view of the water and lush landscape.

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 ￥31,304
￥93,599 total
includes taxes & fees
Jul 27 - Jul 28
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.
Stroll up to this charming home, surrounded by lush greenery and trees, and enjoy the inviting front porch.

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 ￥8,787
￥23,217 total
includes taxes & fees
Jul 28 - Jul 29
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Situated by a serene body of water, this property offers outdoor seating areas and a tranquil atmosphere.

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
Sleeps18*7500SqFt*Bourbon Trial*Themed Spaces*Creek*Hot Tub*Sauna*Luxe Amenties
Experience the expansive interior of this multi-story building, featuring a central open area surrounded by a black iron railing.

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

9.4 out of 10, Exceptional, (3)
"Very enjoyable!"
Sleeps18*7500SqFt*Bourbon Trial*Themed Spaces*Creek*Hot Tub*Sauna*Luxe Amenties
Cozy cabin w/ pool & hot tub! Close to Taylorsville Lake Marina & Bourbon Trails
Relax in a serene hot tub surrounded by lush greenery and trees.

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
Spectacular waterfront house!
Outdoor spa tub

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!
Modern cottage located in the heart of the Bourbon Trail
Enjoy cooking in this well-equipped kitchen with an oven, stovetop, and range hood.

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 ￥15,377
￥28,414 total
includes taxes & fees
Jul 30 - Jul 31
Modern cottage located in the heart of the Bourbon Trail
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Enjoy a compact living space with a kitchenette, large window, and flat-screen TV for a comfortable stay.

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 ￥10,252
￥24,124 total
includes taxes & fees
Aug 16 - Aug 17
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
The Green Cabin-on-The Bourbon Trail
Relax in this serene outdoor seating area with a round table and two chairs, surrounded by lush greenery.

The Green Cabin-on-The Bourbon Trail

9.8 out of 10, Exceptional, (213)
"Liked the big wrap around porch. Cozy living room with huge sectional. Large master bedroom and bath. Good location. Handy to many activities like the bourbon trail and quaint small towns and also the large cities, Frankfort, Lexington and Louisville. Great hosts."
The Green Cabin-on-The Bourbon Trail
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

Hawthorn Suites by Wyndham Louisville East

Hawthorn Suites by Wyndham Louisville East

10/10 Excellent
"We loved our stay and the rooms were big"
Beth 1-night trip
Posted 2 days ago
Hawthorn Suites by Wyndham Louisville East

Frequently asked questions

Can I find vacation rentals in Shelbyville?

Yes, we offer vacation rentals in Shelbyville close to Gallrein Farms, or you can choose a secluded option if you're looking for extra privacy while you relax. The shops and entertainment venues are just a few reasons why travelers like Shelbyville. Make sure you have time to check out the golf courses and cafes during your trip.

What are some of the best vacation rentals in Shelbyville?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: You might want to consider this vacation home rental near Shelbyville, which is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Shelbyville?

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

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 Weissinger Hills Golf Course are other places worth a visit.

What are vacation rentals like in Shelbyville?

Vacation rentals are private properties you can stay in for a short or long stay in Shelbyville. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.