Photo by Lisa Klein

Shelbyville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Shelbyville

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Property grounds

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Cozy Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek
2 bedrooms, free WiFi, bed sheets

Cozy Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek

9.8 out of 10, Exceptional, (37)
"Beautiful cabin centrally located on the Burbon Trail. Enjoyed our stay and would stay again. Winding roads were a little challenging, but worth it."
Cozy Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Interior

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

9.8 out of 10, Exceptional, (72)
"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 ￥100,771
￥192,963 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Exterior

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

10.0 out of 10, Exceptional, (13)
"We had a remarkable time enjoying the entire property. Highly recommend! "
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Exterior detail

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

10.0 out of 10, Exceptional, (113)
"This was a perfect place to stay when visiting distilleries & Lexington. Cozy and beautifully decorated! It’s obvious the owner is a thoughtful person - there are so many little things that you don’t always see in vacation rentals. Would absolutely stay here again!"
The price is ￥20,181
￥30,488 total
includes taxes & fees
Sep 30 - Oct 1
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Dog-Friendly Bourbon Trail Home w/ Speakeasy, Pool, Hot Tub, + Game Room
Exterior

Dog-Friendly Bourbon Trail Home w/ Speakeasy, Pool, Hot Tub, + Game Room

Dog-Friendly Bourbon Trail Home w/ Speakeasy, Pool, Hot Tub, + Game Room
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Outdoor dining

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

10.0 out of 10, Exceptional, (179)
"Way beyond our expectations. We loved our stay!"
The price is ￥22,125
￥47,546 total
includes taxes & fees
Oct 1 - Oct 2
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
Fridge, microwave, oven, stovetop

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

The price is ￥36,259
￥109,964 total
includes taxes & fees
Sep 30 - Oct 1
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
This apartment is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

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

9.2 out of 10, Wonderful, (27)
"Very clean and comfortable! Historic downtown is awesome!"
The price is ￥13,753
￥26,987 total
includes taxes & fees
Sep 30 - Oct 1
This apartment is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!
Fridge, microwave, oven, stovetop

1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!

10.0 out of 10, Exceptional, (80)
"The house is nice and as described. In a great location (if you don’t mind traffic sounds as you are right on a main road). We enjoyed our stay, thanks!"
The price is ￥46,641
￥85,860 total
includes taxes & fees
Oct 27 - Oct 28
1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Exterior

Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

9.6 out of 10, Exceptional, (235)
"The place was awesome and suited the bachelor party perfectly!"
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Bourbon on Broadway
Smart TV

Bourbon on Broadway

2.0 star property
10.0 out of 10, Exceptional, (15)
" wanted to visit. Just a nice place to stay big enough for taking Really enjoyed it. "
The price is ￥17,640
￥33,117 total
includes taxes & fees
Sep 30 - Oct 1
Bourbon on Broadway
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Exterior

High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

10.0 out of 10, Exceptional, (5)
"Remote relaxation"
The price is ￥179,388
￥309,325 total
includes taxes & fees
Oct 15 - Oct 16
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Outdoor spa tub

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

9.8 out of 10, Exceptional, (19)
"Great place good time "
The price is ￥53,682
￥110,892 total
includes taxes & fees
Oct 1 - Oct 2
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
NEW Distiller's Dream - Bourbon Trail Country Fun - 12 min to Bardstown Square
Outdoor dining

NEW Distiller's Dream - Bourbon Trail Country Fun - 12 min to Bardstown Square

10.0 out of 10, Exceptional, (6)
"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 ￥35,878
￥99,538 total
includes taxes & fees
Oct 6 - Oct 7
NEW Distiller's Dream - Bourbon Trail Country Fun - 12 min to Bardstown Square
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65
Outdoor pool

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

10.0 out of 10, Exceptional, (98)
"Everything from top to bottom was fantastic about this property. The location was perfectly located to be able to go into Louisville or Bardstown. "
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65
5BR Very Spacious Home! Perfect for Family!
Fridge, microwave, oven, stovetop

5BR Very Spacious Home! Perfect for Family!

9.2 out of 10, Wonderful, (17)
"My company stayed here during a work trip and we liked it so much we extended our stay. Great area with lots to do!"
The price is ￥24,516
￥77,821 total
includes taxes & fees
Oct 28 - Oct 29
5BR Very Spacious Home! Perfect for Family!
Sleeps18~7500SqFt~Bourbon Trial~Creek~Sauna~Hot Tub~Themed Spaces~Luxe Amenities
Interior

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

9.8 out of 10, Exceptional, (6)
"Our group had an amazing stay at this one-of-a-kind property! The house is incredibly spacious and perfect for large groups, with plenty of room for everyone to spread out and relax. The amenities are top-notch and unlike anything we’ve seen before—especially the speakeasy-style lounge, which quickly became everyone’s favorite hangout spot.The themed rooms were thoughtfully designed and made the stay even more memorable. The layout of the home was very functional, making it easy to gather...
The price is ￥114,563
￥250,304 total
includes taxes & fees
Oct 26 - Oct 27
Sleeps18~7500SqFt~Bourbon Trial~Creek~Sauna~Hot Tub~Themed Spaces~Luxe Amenities
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Exterior

Cozy Tree-Lined Carriage Home - Stay in Serenity!

9.6 out of 10, Exceptional, (15)
"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 ￥9,418
￥23,077 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!
Fridge, microwave, oven, stovetop

Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!

10.0 out of 10, Exceptional, (3)
"Amazing views of the Ohio River and unique design with a lot of character. It was the perfect amount of communal space and privacy for our family of four.Only negatives were some deferred maintenance (leaking fridge, missing remotes, dirty air filter and some outdoor lights out)"
The price is ￥31,393
￥62,986 total
includes taxes & fees
Sep 30 - Oct 1
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelbyville Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Clean, quiet, and super friendly staff"
Ashley 4-night trip
Posted 4 days ago
Comfort Inn & Suites

Find out more about Shelbyville

Find out more about Shelbyville

Search for holiday rentals in Shelbyville on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelbyville using one of the methods below:

  • View our selection of featured holiday rentals in Shelbyville
  • Use the map to find apartments and other holiday homes in the Shelbyville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelbyville while they last

Look no further and take a look at our great range of rental properties in Shelbyville!

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?

Oasis Pool Retreat 8 Bedrooms New Management: Visitors like this Shelbyville vacation home rental. It offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Shelbyville?

Choose from 25 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 Guist Creek Lake State Park 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.