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Vacation Rentals in Shelby County

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Our top choices for Shelby County vacation rentals

A room with a leather sofa, two armchairs, a bed, and a small table with a tray.

1. 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 ￥15,501
￥29,858 total
includes taxes & fees
Oct 25 - Oct 26
Unique Downtown Studio with an Industrial Vibe
A two-story building with a dark facade, a red door, and a sign that reads 'The Stables.'

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 ￥14,889
￥28,888 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥19,929
￥55,498 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥12,812
￥49,895 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A neatly made bed with a blue blanket, two bedside tables with lamps, and floral curtains.

5. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The price is ￥19,929
￥43,199 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥18,651
￥43,786 total
includes taxes & fees
Nov 23 - Nov 24
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A spacious living room with hardwood flooring, a white door with a glass panel, and a dining area with a table and chairs.

7. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is ￥19,297
￥65,623 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥24,042
￥47,707 total
includes taxes & fees
Nov 2 - Nov 3
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A kitchen counter with a vase of flowers, a coffee maker, and a small appliance.

9. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is ￥41,282
￥86,645 total
includes taxes & fees
Nov 22 - Nov 23
Spacious Bourbon retreat near Downtown Louisville!
A wooden deck with a railing, overlooking a well-maintained lawn and trees.

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

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is ￥29,578
￥57,742 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
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 ￥34,559
￥69,516 total
includes taxes & fees
Nov 5 - Nov 6
Beautiful restored Victorian farmhouse
A house with a covered porch, outdoor seating, and a grill area.

12. 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 ￥28,684
￥121,772 total
includes taxes & fees
Nov 2 - Nov 3
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 covered outdoor patio with wicker furniture, a fire pit, and string lights.

13. 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 ￥30,922
￥91,601 total
includes taxes & fees
Oct 26 - Oct 27
Kentucky Bourbon Trail: Hot Tub & Game Room
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

14. 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 ￥41,140
￥92,792 total
includes taxes & fees
Oct 27 - Oct 28
the bourbon barrel escape HotTub Game Room pets ok
A wooden deck with rocking chairs and a bench, surrounded by trees with autumn foliage.

15. 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 ￥42,706
￥131,857 total
includes taxes & fees
Oct 27 - Oct 28
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
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, (23 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is ￥76,700
￥93,412 total
includes taxes & fees
Nov 2 - Nov 3
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A log cabin with a covered porch, large windows, and a well-maintained front yard.

17. 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, (11 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is ￥71,177
￥90,486 total
includes taxes & fees
Oct 26 - Oct 27
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.

18. *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, (9 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.
*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.

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 ￥112,422
￥221,589 total
includes taxes & fees
Nov 2 - Nov 3
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, (12 reviews)
"Nice stay"
United States
Jackie S.
The price is ￥147,483
￥262,184 total
includes taxes & fees
Nov 23 - Nov 24
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.
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Top Shelby County Hotel Reviews

Cambria Hotel Louisville Downtown-Whiskey Row

Cambria Hotel Louisville Downtown-Whiskey Row

10/10 Excellent
"Wi-Fi was slow & intermittent"
Kenneth 3-night trip
Posted less than an hour ago
Cambria Hotel Louisville Downtown-Whiskey Row

Find out more about Shelby County

Vacation Apartments in Shelby County

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