Holiday Rentals in Shelby County

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Our top choices for Shelby County holiday rentals

9.8 out of 10, Exceptional, (8)
"This was an excellent option as a base to organize some outings to distilleries. We focused on distilleries in Frankfort and Louisville, so Shke yvulle was a great in between stop. The only snafu of the trip was the door code didn't work on arrival, but the owner responded quickly to text to get us in. The house is charming and clean and very quiet outside of the random trains. But if you make use of the ear plugs thoughtfully sprinkled through the bedrooms, the trains aren't much of a problem....
United States
Mike L.
The price is €305
includes taxes & fees
20 Jan - 21 Jan 2026
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
9.4 out of 10, Exceptional, (13)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is €383
includes taxes & fees
1 Jan - 2 Jan 2026
Beautiful restored Victorian farmhouse
9.8 out of 10, Exceptional, (30)
"Cool place to stay & great location"
United States
Amy B.
The price is €160
includes taxes & fees
21 Jan - 22 Jan 2026
Unique Downtown Studio with an Industrial Vibe
8.8 out of 10, Excellent, (9)
"Clean, quiet and a great location. "
United States
Marla B.
The price is €276
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
10.0 out of 10, Exceptional, (19)
"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 €160
includes taxes & fees
11 Jan - 12 Jan 2026
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay. It's a great cozy and comfortable place that's secluded and private. Iris was a great host. "
United States
Madison W.
The price is €532
includes taxes & fees
4 Jan - 5 Jan 2026
Fall & Winter Retreat: Hot Tub, Bourbon, & Pets!
9.8 out of 10, Exceptional, (18)
"Great location, responsive hosts, fantastic property!"
United States
Timothy S.
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Holiday Home in Shelbyville

Hitching Post on the Bourbon Trl
10.0 out of 10, Exceptional, (3)
"Fantastic location for a large family or group of friends. The layout of the house provided for plenty of privacy in a large group, and the game room in the basement was a wonderful place to socialize. Location is great for visiting the bourbon trail and Louisville."
United States
Joe O.
Hitching Post on the Bourbon Trl
2.0 star property
10.0 out of 10, Exceptional, (16)
"Overall great value and accommodations. Would highly recommend this property."
United States
Chad K.
The price is €523
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub, Bourbon Trail, Speakeasy, Firepit, GameRm
10.0 out of 10, Exceptional, (16)
"Our extended family (4 couples) stayed here for a weekend getaway and it was very nice! Each couple got their own room! All the rooms and main areas were clean and very comfortable. We actually thought the house was nicer than the pictures led on. "
United States
Bethany & Taylor L.
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
10.0 out of 10, Exceptional, (9)
"Great location, close to Frankfort, Louisville and Lexington. Theater room was amazing! "
United States
Nicole D.
The price is €1,797
includes taxes & fees
31 Dec - 1 Jan 2026
Luxury lodge in the heart of the Bluegrass
*NEW* LUXURY HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-6 BEDS/5 BATHS-5 KING BEDS
10.0 out of 10, Exceptional, (3)
"Great place to stay. Highly recommend"
United States
Jackson D.
The price is €1,312
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Mobile Home in Lawrenceburg

Bourbon Trail: Caboose on the Farm
10.0 out of 10, Exceptional, (38)
"Staying in the Caboose on the Farm was such a fun and relaxing escape. The space was clean, cozy and full of charm with beautiful views and friendly animals. It was the perfect mix of comfort and nature. Highly recommend for anyone looking for a unique getaway!"
United States
Lindsey
Bourbon Trail: Caboose on the Farm
3.0 star property
10.0 out of 10, Exceptional, (1)
"Amy was wonderful and went above and beyond to make sure we had a great stay. She even left pancakes w/syrup for breakfast and pasta w/sauce in case we didn’t have time to go to the store! It’s the small things that really stick out such as leaving a bowl of snacks, a few beers in the fridge, a bottle of wine, fully stocked medicine cabinet in case you forgot something. She even put food and water out for the dog along with toys and a blanket! We loved being there and it was such a beautiful...
United States
Robin
The price is €293
includes taxes & fees
2 Jan - 3 Jan 2026
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Aparthotel in Tyler Park

The Bellwether Hotel
3.5 star property
8.8 out of 10, Excellent, (32)
"Spectacular room, fabulous decor, tasty cookies, quiet stay "
United States
Mark
The price is €113
includes taxes & fees
2 Jan - 3 Jan 2026
The Bellwether Hotel

Aparthotel in Downtown Louisville

Stellar Suites
4.5 star property
9.6 out of 10, Exceptional, (117)
"Clean and great location "
United States
Greg
The price is €161
includes taxes & fees
13 Jan - 14 Jan 2026
Stellar Suites

Aparthotel in Downtown Louisville

The Reserve on Main
4.0 star property
10.0 out of 10, Exceptional, (1)
"Incredible stay. This stay was clean and inspiring for anyone wishing to take a break and recharge. We highly recommend this stay to everyone staying in the city. "
Canada
georgios
The price is €205
includes taxes & fees
7 Jan - 8 Jan 2026
The Reserve on Main
9.8 out of 10, Exceptional, (62)
"Host was responsive to all messages. The small home we stayed in was so cozy and clean. Directions on how to get there were clear and easy to follow. 10/10 would recommend."
United States
Haley V.
The price is €200
includes taxes & fees
31 Dec - 1 Jan 2026
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
10.0 out of 10, Exceptional, (47)
"Located near lovely parks on the river. There is very little traffic in this area, yet you are close to downtown.We've stayed here twice because it is so clean, comfortable, stylish, and relaxing. "
United States
Debbie B.
The price is €206
includes taxes & fees
3 Jan - 4 Jan 2026
Carriage House, 7 minutes from downtown Louisville
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

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Holiday Homes in Shelby County

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