Lodging Image

Vacation Rentals in Shelby County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Our top choices for Shelby County vacation rentals

A living room with a TV, a wooden entertainment unit, a round coffee table, and a sofa.

1. 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, (21 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 ￥14,950
￥29,006 total
includes taxes & fees
Oct 4 - Oct 5
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A bar area with a black bar counter, stools, and a large horseshoe-shaped metal object on the wall.

2. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 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 ￥14,163
￥27,958 total
includes taxes & fees
Oct 4 - Oct 5
Unique Downtown Studio with an Industrial Vibe
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 ￥19,836
￥55,239 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥19,836
￥59,244 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A porch with two wooden chairs and a table, white siding, and a window.

5. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The Shelby House | Historic Charm, Modern Comfort
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

6. 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 ￥18,727
￥43,263 total
includes taxes & fees
Oct 4 - Oct 5
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

7. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is ￥23,291
￥70,491 total
includes taxes & fees
Oct 14 - Oct 15
Haven of the Bluegrass | Bourbon Trail Getaway!
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, (50 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is ￥27,540
￥51,846 total
includes taxes & fees
Oct 29 - Oct 30
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

9. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.2 out of 10, Wonderful, (15 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is ￥34,700
￥70,151 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful restored Victorian farmhouse
A house with a covered porch, outdoor seating, and a grill area.

10. Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space

Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Shelbyville
The price is ￥26,832
￥118,912 total
includes taxes & fees
Oct 4 - Oct 5
Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
A wooden deck with rocking chairs and a bench, surrounded by trees with autumn foliage.

11. 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.
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
A modern kitchen with a central island, bar stools, and a dining table with blue chairs.

12. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is ￥28,799
￥70,453 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Bourbon retreat near Downtown Louisville!
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

13. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is ￥40,948
￥87,277 total
includes taxes & fees
Oct 19 - Oct 20
the bourbon barrel escape HotTub Game Room pets ok
A log cabin with a covered porch, large windows, and a well-maintained front yard.

14. 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
9.8 out of 10, Exceptional, (10 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is ￥72,390
￥92,130 total
includes taxes & fees
Oct 21 - Oct 22
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

15. *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
9.6 out of 10, Exceptional, (7 reviews)
"We had a fantastic holiday weekend at this property - Two families (4 adults, 4 kids) stayed with plenty of room and amenities. This house could have easily slept more. Communication from the host was clear and prompt. The kids absolutely loved the game room and adults enjoyed the ample living spaces on both the main floor and the basement. Although we didn't use the pool given the time of year, the hot tub, sauna, and fire pit were great! Our kids loved seeing the horses all around...
United States
Justin C.
The price is ￥49,414
￥141,464 total
includes taxes & fees
Oct 4 - Oct 5
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A white building with a porch, columns, and a covered entrance.

16. Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (17 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
The price is ￥61,185
￥122,921 total
includes taxes & fees
Oct 8 - Oct 9
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

17. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Shelbyville
10.0 out of 10, Exceptional, (23 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is ￥80,592
￥102,250 total
includes taxes & fees
Oct 5 - Oct 6
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A living room with a sectional sofa, a dining table, and a ceiling fan.

18. Peaceful 6-bedroom house in charming Bagdad

Peaceful 6-bedroom house in charming Bagdad
Bagdad
The price is ￥85,263
￥208,396 total
includes taxes & fees
Oct 14 - Oct 15
Peaceful 6-bedroom house in charming Bagdad
A log cabin with a stone chimney, multiple windows, and a porch with outdoor seating.

19. 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 traveler
The price is ￥196,713
￥329,113 total
includes taxes & fees
Oct 28 - Oct 29
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.

20. 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, (11 reviews)
"Nice stay"
United States
Jackie S.
The price is ￥132,871
￥244,081 total
includes taxes & fees
Oct 6 - Oct 7
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
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 Shelby County Hotel Reviews

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

10/10 Excellent
"3 men working desk that I came in contact with and they were great. Made thru third party but. Received well by associates. Should have breakfast."
Robin 1-night trip
Posted 5 hours ago
Holiday Inn Louisville Airport South by IHG

Find out more about Shelby County

Vacation Apartments in Shelby County

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

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

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