Book Holiday Homes in Kentucky

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Featured Holiday Homes in Kentucky

Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace

Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace

Frankfort
The price is AU$471 per night from 24 Feb to 25 Feb
AU$471
includes taxes & fees
24 Feb - 25 Feb
With a stay at this vacation home, you'll be centrally located in Frankfort, within a 5-minute drive of Buffalo Trace Distillery and Liberty Hall.
Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

Frankfort
With a stay at this vacation home in Frankfort, you'll be on a river, within a 10-minute drive of Buffalo Trace Distillery and Greenhill Cemetery.
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Shelbyville
With a stay at this vacation home in Shelbyville, you'll be within a 15-minute drive of Gallrein Farms and Guist Creek Lake State Park.
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
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Rare 4 Bedroom Near Ark Encounter

Rare 4 Bedroom Near Ark Encounter

Dry Ridge
With a stay at this vacation home in Dry Ridge, you'll be within a 10-minute drive of Ark Encounter and Dry Ridge Outlet Mall.
Rare 4 Bedroom Near Ark Encounter
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

Lexington
With a stay at this vacation home in Lexington (Castlewood), you'll be a 5-minute drive from Rupp Arena and 5 minutes from University of Kentucky.
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Home Sweet Hayden - 4 beds/3 Full Bath in East End

Home Sweet Hayden - 4 beds/3 Full Bath in East End

Louisville
With a stay at this vacation home in Louisville, you'll be within a 15-minute drive of Louisville Zoo and Louisville Mega Cavern.
Home Sweet Hayden - 4 beds/3 Full Bath in East End
Isla's Landing - Charming Historic 1940s Home

Isla's Landing - Charming Historic 1940s Home

Lexington
With a stay at this vacation home, you'll be centrally located in Lexington, within a 5-minute drive of The Red Mile Racetrack and University of Kentucky.
Isla's Landing - Charming Historic 1940s Home
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Shepherdsville
The price is AU$945 per night from 23 Mar to 24 Mar
AU$945
includes taxes & fees
23 Mar - 24 Mar
Located in Shepherdsville, this vacation home is in a rural location, within a 10-minute drive of McNeely Lake Park and Fairmount Falls Park.
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park

Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park

Mammoth Cave
The price is AU$1,094 per night from 23 Feb to 24 Feb
AU$1,094
includes taxes & fees
23 Feb - 24 Feb
With a stay at this vacation home in Mammoth Cave, you'll be a 1-minute drive from Mammoth Cave National Park and 6 minutes from Green River.
Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park
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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.

Kentucky Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kentucky vacation homes are the perfect way for you to wing it.

Holiday houses in Kentucky let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kentucky in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kentucky adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kentucky with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kentucky vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kentucky Holiday Homes essential information

Accommodation
2569 Holiday Homes
Lowest Price
AU$165
Highest Price
AU$1,094
Popular accommodation
Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace, "Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail, Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, Rare 4 Bedroom Near Ark Encounter, This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY., Home Sweet Hayden - 4 beds/3 Full Bath in East End, Isla's Landing - Charming Historic 1940s Home, Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!, Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park

Top trending hotels in Kentucky

Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
The price is AU$357 per night from 27 Feb to 28 Feb
AU$357
includes taxes & fees
27 Feb - 28 Feb
With a stay at Omni Louisville Hotel, you'll be centrally located in Louisville, steps from Fourth Street Live! and 4 minutes by foot from Kentucky International ...
Omni Louisville Hotel
Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 16 Mar to 17 Mar
AU$267
includes taxes & fees
16 Mar - 17 Mar
Galt House Hotel Trademark Collection by Wyndham is in the heart of Louisville, within a 5-minute walk of KFC Yum Center and Kentucky International Convention ...
Galt House Hotel Trademark Collection by Wyndham
Radisson Hotel Cincinnati Riverfront

Radisson Hotel Cincinnati Riverfront

3.5 out of 5
668 W 5th St, Covington, KY
Fully refundable
The price is AU$165 per night from 2 Mar to 3 Mar
AU$165
includes taxes & fees
2 Mar - 3 Mar
With a stay at Radisson Hotel Cincinnati Riverfront, you'll be centrally located in Covington, within a 5-minute drive of Great American Ball Park and Paycor ...
Radisson Hotel Cincinnati Riverfront
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Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$251 per night from 9 Mar to 10 Mar
AU$251
includes taxes & fees
9 Mar - 10 Mar
Hilton Lexington/Downtown is centrally located in Lexington, a 3-minute walk from Lexington Opera House and 5 minutes by foot from Rupp Arena.
Hilton Lexington/Downtown
Don't see what you're looking for?
See all available properties in Kentucky
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.