Vacation Rentals in Shelby County

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Top Vacation Rentals in Shelby County

Cottage in Shelbyville

9.4 out of 10, Exceptional, (13)
"This property was just as described. Communication with the host was excellent. We’ll stay here again!"
United States
Carla R.
$396 nightly
The price is $440
Dec 15 - Dec 16
Total with taxes and fees
Beautiful restored Victorian farmhouse

Cottage in Shelbyville

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.
$259 nightly
The price is $288
Dec 16 - Dec 17
Total with taxes and fees
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Vacation Home in Bagdad

10.0 out of 10, Exceptional, (22)
"We loved this place. It is beautiful and so peaceful. We visited Frankfort, Versailles, Lexington and Louisville while we were here. It was wonderful."
United States
Shawnee W.
$536 nightly
The price is $595
Dec 7 - Dec 8
Total with taxes and fees
Fall & Winter Retreat: Hot Tub, Bourbon, & Pets!

Vacation Home in Shelbyville

9.8 out of 10, Exceptional, (18)
"Great location, responsive hosts, fantastic property!"
United States
Timothy S.
$440 nightly
The price is $490
Dec 7 - Dec 8
Total with taxes and fees
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Apartment in Shelbyville

9.8 out of 10, Exceptional, (30)
"Had a great stay, not to far from Louisville. "
Canada
Janet E.
$175 nightly
The price is $194
Dec 14 - Dec 15
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe

Apartment in Shelbyville

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.
$180 nightly
The price is $200
Dec 9 - Dec 10
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Vacation Home in Shelbyville

2.0 star property
10.0 out of 10, Exceptional, (15)
"House was immaculate, communication was wonderful, will book again! "
United States
Deborah B.
$536 nightly
The price is $595
Dec 14 - Dec 15
Total with taxes and fees
Hot Tub | Bourbon Trail | Speakeasy | Game Rm

Vacation Home in Bagdad

9.4 out of 10, Exceptional, (10)
"I had my bachelor party here and it was the perfect place to get away!"
United States
Kyser M.
$455 nightly
The price is $506
Dec 10 - Dec 11
Total with taxes and fees
Modern Farmhouse Near Distilleries! Hot tub, GameRoom, Firepit, Luxury, 5-Acres!

Cabin in Shelbyville

10.0 out of 10, Exceptional, (3)
"Great place to stay. Highly recommend"
United States
Jackson D.
$1,147 nightly
The price is $1,277
Dec 7 - Dec 8
Total with taxes and fees
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Vacation Home in Bagdad

$833 nightly
The price is $918
Dec 7 - Dec 8
Total with taxes and fees
*NEW* LUXURY HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-6 BEDS/5 BATHS-5 KING BEDS

Vacation Home in Waddy

8.8 out of 10, Excellent, (9)
"Clean, quiet and a great location. "
United States
Marla B.
$305 nightly
The price is $323
Dec 9 - Dec 10
Total with taxes and fees
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cabin in Waddy

10.0 out of 10, Exceptional, (8)
"Great location, close to Frankfort, Louisville and Lexington. Theater room was amazing! "
United States
Nicole D.
$1,893 nightly
The price is $2,107
Dec 7 - Dec 8
Total with taxes and fees
Luxury lodge in the heart of the Bluegrass

Mobile Home in Lawrenceburg

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
$225 nightly
The price is $244
Dec 7 - Dec 8
Total with taxes and fees
Bourbon Trail: Caboose on the Farm

Aparthotel in Tyler Park

3.5 star property
8.8 out of 10, Excellent, (32)
"Spectacular room, fabulous decor, tasty cookies, quiet stay "
United States
Mark
$108 nightly
The price is $126
Dec 8 - Dec 9
Total with taxes and fees
The Bellwether Hotel

Aparthotel in Downtown Louisville

4.5 star property
9.6 out of 10, Exceptional, (117)
"Clean and great location "
United States
Greg
$154 nightly
The price is $179
Dec 23 - Dec 24
Total with taxes and fees
Stellar Suites

Aparthotel in Downtown Louisville

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
$168 nightly
The price is $188
Dec 8 - Dec 9
Total with taxes and fees
The Reserve on Main

Cabin in Louisville

9.8 out of 10, Exceptional, (138)
"Our host were phenomenal. Made us feel right at home. I would highly recommend this place to anybody.!!"
United States
Corey D.
$316 nightly
The price is $366
Dec 7 - Dec 8
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Condo in Frankfort

8.8 out of 10, Excellent, (97)
"We enjoyed our stay while we were down for Breyer Fest. It was close to places we wanted to go and quiet. We would definitely stay here again."
United States
Jacob Y.
$140 nightly
The price is $165
Dec 7 - Dec 8
Total with taxes and fees
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Cottage in New Albany

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
$339 nightly
The price is $380
Jan 2 - Jan 3, 2026
Total with taxes and fees
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Vacation Home in Frankfort

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean and communication with host was excellent. Would recommend to anyone. "
United States
Chuck F.
$297 nightly
The price is $350
Dec 7 - Dec 8
Total with taxes and fees
Miss Reba's Love is a charming house with a warm Kentucky feel.
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

Find out more about Shelby County

Discover your perfect Shelby County vacation rental with Expedia

How many vacation rentals are available in Shelby County?


Expedia has plenty of vacation rentals to choose from in and around  Shelby County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Shelby County?


The selection of Shelby County vacation rentals we have selected for you start as low as $126 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Shelby County?


Vacation rentals in Shelby County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Shelby County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Shelby County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Shelby County?


Find vacation rentals in Shelby County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Shelby County.  


What amenities are available in a vacation rental in Shelby County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Shelby County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Shelby County?   


Everytime is a great time to head to Shelby County! Staying in a Shelby County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Shelby County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Shelby County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Shelby County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Shelby County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.