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Shelby County Holiday Rentals

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Our top choices for Shelby County holiday rentals

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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, (20 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 HK$745
HK$1,437 total
includes taxes & fees
15 Sept - 16 Sept
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Bar (on property)

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 HK$706
HK$1,332 total
includes taxes & fees
14 Sept - 15 Sept
Unique Downtown Studio with an Industrial Vibe
Coffee/tea maker, fridge, microwave, oven

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 HK$988
HK$2,630 total
includes taxes & fees
14 Sept - 15 Sept
Quiet Downtown Maple Cottage Gem
Coffee/tea maker, fridge, microwave, oven

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 HK$508
HK$2,214 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Private kitchen

5. 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 HK$933
HK$2,156 total
includes taxes & fees
21 Sept - 22 Sept
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
Exterior

6. 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, (48 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is HK$1,231
HK$2,304 total
includes taxes & fees
14 Sept - 15 Sept
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Coffee/tea maker, fridge, microwave, oven

7. 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 HK$1,729
HK$3,339 total
includes taxes & fees
14 Sept - 15 Sept
Beautiful restored Victorian farmhouse
TV

8. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is HK$1,592
HK$4,068 total
includes taxes & fees
30 Sept - 1 Oct
Haven of the Bluegrass | Bourbon Trail Getaway!
Exterior

9. Your Kentucky Bourbon Trail stay 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 with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Shelbyville
The price is HK$1,337
HK$5,337 total
includes taxes & fees
14 Sept - 15 Sept
Your Kentucky Bourbon Trail stay with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Outdoor dining

10. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is HK$2,040
HK$4,583 total
includes taxes & fees
28 Sept - 29 Sept
the bourbon barrel escape HotTub Game Room pets ok
Terrace/patio

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.
The price is HK$2,141
HK$6,075 total
includes taxes & fees
14 Sept - 15 Sept
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
Exterior

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

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Shelbyville
9.8 out of 10, Exceptional, (9 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is HK$3,137
HK$3,989 total
includes taxes & fees
29 Sept - 30 Sept
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Exterior

13. 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 HK$3,049
HK$6,126 total
includes taxes & fees
17 Sept - 18 Sept
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
A heated pool

14. *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, (5 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 HK$2,604
HK$7,222 total
includes taxes & fees
14 Sept - 15 Sept
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Interior

15. Peaceful 6-bedroom house in charming Bagdad

Peaceful 6-bedroom house in charming Bagdad
Bagdad
The price is HK$4,630
HK$10,870 total
includes taxes & fees
15 Sept - 16 Sept
Peaceful 6-bedroom house in charming Bagdad
Outdoor spa tub

16. 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 HK$3,811
HK$4,623 total
includes taxes & fees
14 Sept - 15 Sept
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Exterior

17. 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 HK$10,446
HK$16,444 total
includes taxes & fees
14 Sept - 15 Sept
Luxury lodge in the heart of the Bluegrass
Smart TV, fireplace, DVD player

18. 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)
"Great place to stay. Highly recommend"
United States
Jackson D.
The price is HK$6,956
HK$12,587 total
includes taxes & fees
7 Oct - 8 Oct
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
Interior

19. 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, (108 reviews)
"Perfect location for the Bourbon Trail. Nice, clean, and affordable. 10 out of 10, would do it again!"
United States
Dwight K.
The price is HK$549
HK$1,292 total
includes taxes & fees
14 Sept - 15 Sept
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Interior

20. Capital City Condo #10

Capital City Condo #10
Frankfort
8.4 out of 10, Very good, (9 reviews)
"Such a great little place. Hosts are wonderful!"
United States
Amanda L.
The price is HK$549
HK$1,292 total
includes taxes & fees
14 Sept - 15 Sept
Capital City Condo #10
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
"Room was fantastic as well as the casino! Thoroughly enjoyed it! Oliver’s restaurant was wonderful too!"
Jeannette 1-night trip
Posted 4 hours ago
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)