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Shelby County Vacation Rentals

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Our top choices for Shelby County vacation rentals

A bar area with stools, a coffee machine, and a large metal horseshoe decoration on the wall.

1. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is CA $134
CA $246 total
includes taxes & fees
Dec 8 - Dec 9
Unique Downtown Studio with an Industrial Vibe
A kitchen with a gas stove, a coffee maker, and built-in ovens.

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

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (22 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is CA $134
CA $246 total
includes taxes & fees
Dec 8 - Dec 9
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A modern kitchen with a dining area, built-in shelves, and a green sofa in the living room.

3. Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is CA $178
CA $470 total
includes taxes & fees
Nov 17 - Nov 18
Quiet Downtown Maple Cottage Gem
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

4. Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
9.0 out of 10, Wonderful, (12 reviews)
"Excellent stay and a beautiful property. Perfect for our needs no complaints."
United States
Anthony T.
The price is CA $123
CA $580 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A hallway with a green door, a large mirror, a wooden console table, and a framed picture on the wall.

5. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The price is CA $178
CA $373 total
includes taxes & fees
Nov 15 - Nov 16
The Shelby House | Historic Charm, Modern Comfort
A modern kitchen with white cabinetry, a fireplace, and a bar area with stools.

6. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is CA $198
CA $749 total
includes taxes & fees
Nov 29 - Nov 30
Haven of the Bluegrass | Bourbon Trail Getaway!
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

7. Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
Waddy
10.0 out of 10, Exceptional, (2 reviews)
"The place was great. Tucked away off the main highway and between bourbon country’s best. Well stocked amenities and little things provided that were a great touch. Will be back again!"
United States
Daniel H.
The price is CA $168
CA $374 total
includes taxes & fees
Nov 19 - Nov 20
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

8. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is CA $210
CA $399 total
includes taxes & fees
Nov 15 - Nov 16
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A modern kitchen with a central island, stainless steel appliances, and bar stools.

9. Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is CA $230
CA $449 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A modern kitchen with a stainless steel sink, a built-in faucet, and a window overlooking a deck with outdoor seating.

10. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is CA $273
CA $819 total
includes taxes & fees
Nov 15 - Nov 16
Spacious Bourbon retreat near Downtown Louisville!
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

11. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (16 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is CA $311
CA $571 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful restored Victorian farmhouse
A covered outdoor patio with wicker furniture, a fire pit, and string lights.

12. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
The price is CA $231
CA $751 total
includes taxes & fees
Nov 11 - Nov 12
Kentucky Bourbon Trail: Hot Tub & Game Room
A modern living room with a stone accent wall, a grey sofa, a wooden coffee table, and a ceiling fan.

13. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"The host was super helpful and friendly! We had everything that was advertised. The House was cozy and fun for a group of friends. Wonderful stay!"
United States
Breanna N.
The price is CA $408
CA $854 total
includes taxes & fees
Nov 16 - Nov 17
the bourbon barrel escape HotTub Game Room pets ok
A kitchen with a central island, wooden ceiling, and bar stools.

14. On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace

On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
Waddy
9.0 out of 10, Wonderful, (7 reviews)
"Some friends and I were in town for a bourbon tour and a Keeneland visit. The property is gorgeous, and centrally located between Lexington and Louisville, The house is immaculate and perfect for a trip like this. The host is excellent, and every detail of the property was thought of. Our stay was over and above anything we imagined. Thank You!! "
United States
Timothy S.
The price is CA $357
CA $1,039 total
includes taxes & fees
Nov 11 - Nov 12
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
A log cabin with a covered porch, large windows, and a well-maintained front yard.

15. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Shelbyville
10.0 out of 10, Exceptional, (12 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is CA $718
CA $828 total
includes taxes & fees
Nov 11 - Nov 12
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

16. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Shelbyville
10.0 out of 10, Exceptional, (25 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is CA $747
CA $902 total
includes taxes & fees
Nov 15 - Nov 16
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

17. *NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Bagdad
9.8 out of 10, Exceptional, (11 reviews)
"My family & I had a great time at the house. My grandkids loved the pool. It was a very enjoyable stay."
United States
LORI T.
The price is CA $470
CA $1,237 total
includes taxes & fees
Nov 15 - Nov 16
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A log cabin with a stone chimney, multiple windows, and a porch with outdoor seating.

18. Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveller
The price is CA $1,053
CA $1,856 total
includes taxes & fees
Nov 16 - Nov 17
Luxury lodge in the heart of the Bluegrass
A cozy cabin interior with a stone fireplace, a leather sofa, and a large window offering a view of the outdoors.

19. Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
Shelbyville
10.0 out of 10, Exceptional, (13 reviews)
"Nice stay"
United States
Jackie S.
The price is CA $1,379
CA $2,307 total
includes taxes & fees
Dec 8 - Dec 9
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
A living room with a sofa, a coffee table, a rug, and a bookshelf.

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

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Frankfort
8.8 out of 10, Excellent, (110 reviews)
"It was a great place to stay & conveniently located to lots of restaurants & distilleries."
United States
Darby D.
The price is CA $99
CA $219 total
includes taxes & fees
Nov 17 - Nov 18
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 Shelby County Hotel Reviews

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

10/10 Excellent
"Perfect stay for Bourbon and Beyond. Enjoyed the casino a lot before heading to the venue each day. Room is clean, bed is comfortable, appreciated waters already stocked In the fridge. This was our second year there in a row. Didn’t disappoint!"
marie 4-night trip
Posted 3 hours ago
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Find out more about Shelby County

Everything you need to know about Shelby County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelby County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelby County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shelby County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelby County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelby County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelby County vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shelby County rentals

At Expedia, we put the best Shelby County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shelby County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelby County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelby County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.