Kentucky vacation rentals

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Top-rated vacation rentals in Kentucky

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Train in Lawrenceburg
Bourbon Trail: Caboose on the Farm
Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!
Aug 30 – Sep 6Individual Host,
€ 149 per night
4.98 out of 5 average rating, 247 reviews
Guest favorite
Home in Stamping Ground
Buffalo Springs Distilling Company
On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week
Dec 9 – 16Individual Host,
€ 160 per night
4.97 out of 5 average rating, 594 reviews
Guest favorite
Cottage in Wilmore
River House - Cottage with KY River View & Access
Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.
Jul 28 – Aug 4Individual Host,
€ 136 per night
4.97 out of 5 average rating, 156 reviews

Popular amenities for Kentucky vacation rentals

Kentucky fishing vacation rentals

Guest favorite
Cabin in Dixon
Crouse’s North Ninety Lake House
Nov 29 – Dec 6Individual Host,
€ 154 per night
4.96 out of 5 average rating, 228 reviews
Guest favorite
Guest suite in Albany
“Page's Legacy "Winter Lake Getaway"
Nov 2 – 9Individual Host,
€ 126 per night
4.98 out of 5 average rating, 201 reviews
Guest favorite
Cottage in Dry Ridge
Lake Getaway for 2 in country/Near Ark Encounter
Aug 16 – 21Individual Host,
€ 197 per night
5.0 out of 5 average rating, 149 reviews
Guest favorite
Cabin in Louisville
Captain's Cabin:Historic Romantic by Bourbon Trail
Feb 18 – 25Individual Host,
€ 285 per night
4.96 out of 5 average rating, 297 reviews
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
Oct 5 – 12Individual Host,
€ 184 per night
4.95 out of 5 average rating, 199 reviews
Guest favorite
Home in Lewisburg
Charming Lakefront A-Frame with 4 Adult Kayaks
Nov 15 – 22Professional Host,
€ 149 per night
4.98 out of 5 average rating, 104 reviews
Superhost
Cabin in Falls of Rough
Rough River Lake Cabin close to ramp pet friendly!
Nov 30 – Dec 7Individual Host,
€ 91 per night
4.78 out of 5 average rating, 148 reviews
Guest favorite
Cabin in Mount Eden
Bourbon Country Cottage
Jun 1 – 8Individual Host,
€ 162 per night
4.97 out of 5 average rating, 103 reviews
Guest favorite
Cabin in Burnside
Cumberland Cabin Get Away
Jun 2 – 9Individual Host,
€ 96 per night
4.88 out of 5 average rating, 128 reviews
Superhost
Cottage in Versailles
River Front Cottage on the Bourbon Trail
Feb 7 – 14Professional Host,
€ 157 per night
4.88 out of 5 average rating, 175 reviews
Guest favorite
Cottage in Pleasureville
The Cozy Cottage on One Goat Farm
Jun 23 – 30Individual Host,
€ 115 per night
4.99 out of 5 average rating, 174 reviews
Guest favorite
Cabin in Louisa
Heavens Porch - Eastern KY Luxury Cabin Rental
Aug 12 – 19Individual Host,
€ 181 per night
4.88 out of 5 average rating, 132 reviews

Home rentals in Kentucky

Guest favorite
Home in Wayne County
Nancy Kentucky - The Faubush Cabin
Apr 25 – May 2Individual Host,
€ 121 per night
4.99 out of 5 average rating, 109 reviews
Guest favorite
Home in Berea
Berea Painter's Cottage
Apr 28 – May 5Individual Host,
€ 111 per night
4.92 out of 5 average rating, 623 reviews
Guest favorite
Home in Springfield
Cabin Chic on Main
Aug 16 – 23Individual Host,
€ 88 per night
4.98 out of 5 average rating, 525 reviews
Guest favorite
Home in Versailles
Quaint little farm house close to Keeneland/horses
Jan 10 – 17Individual Host,
€ 140 per night
4.94 out of 5 average rating, 115 reviews
Guest favorite
Home in Bardstown
Creekview Farm: Bourbon, Horses, and Sunsets
Aug 29 – Sep 5Individual Host,
€ 135 per night
4.95 out of 5 average rating, 451 reviews
Guest favorite
Home in Grand Rivers
Seclusion with the Lake a step away....
Dec 23 – 30Individual Host,
€ 94 per night
4.98 out of 5 average rating, 507 reviews
Guest favorite
Home in Paducah
902 historic brick shotgun house
Jul 25 – Aug 1Individual Host,
€ 68 per night
4.97 out of 5 average rating, 210 reviews
Guest favorite
Home in Harrodsburg
Kentucky Horse Farm Barndo On The Bourbon Trail
Jan 8 – 15Individual Host,
€ 109 per night
4.92 out of 5 average rating, 197 reviews
Guest favorite
Home in Covington
Hot Tub Riverfront Bungalow w/Stunning Views
Jan 31 – Feb 7Individual Host,
€ 161 per night
4.98 out of 5 average rating, 143 reviews
Guest favorite
Home in Science Hill
TT’s Treehouse
Jan 10 – 17Individual Host,
€ 135 per night
4.97 out of 5 average rating, 105 reviews
Guest favorite
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
Sep 29 – Oct 6Individual Host,
€ 83 per night
4.95 out of 5 average rating, 131 reviews
Guest favorite
Home in Raywick
Bourbon Trail Country Farmhouse
Nov 21 – 28Individual Host,
€ 141 per night
5.0 out of 5 average rating, 165 reviews

Lakefront home rentals in Kentucky

Guest favorite
Home in Lewisburg
Laid Back Lake House w/ hot tub and private dock❗️
Sep 1 – 8Individual Host,
€ 251 per night
4.93 out of 5 average rating, 108 reviews
Guest favorite
Home in Brandenburg
Luxury lakehouse retreat with picturesque views
Sep 18 – 25Individual Host,
€ 649 per night
4.95 out of 5 average rating, 236 reviews
Guest favorite
Home in Dry Ridge
Custom Log Home on Lake Williamstown. Near Ark.
Sep 16 – 23Individual Host,
€ 718 per night
5.0 out of 5 average rating, 159 reviews
Superhost
Home in Russell Springs
Driftwood Cottage with HotTub on Lake Cumberland
Oct 16 – 23Individual Host,
€ 205 per night
4.78 out of 5 average rating, 197 reviews
Guest favorite
Home in Somerset
Lakeview Blue
Aug 13 – 20Individual Host,
€ 237 per night
4.88 out of 5 average rating, 112 reviews
Guest favorite
Home in Glasgow
Tranquil Cabin on Barren River Lake
Nov 11 – 18Individual Host,
€ 201 per night
4.91 out of 5 average rating, 127 reviews
Guest favorite
Home in Prospect
The River House
Jan 20 – 27Individual Host,
€ 311 per night
4.94 out of 5 average rating, 207 reviews
Guest favorite
Home in Louisville
The Lakehouse at Progress Park in Derby City
Nov 15 – 22Professional Host,
€ 308 per night
4.98 out of 5 average rating, 228 reviews
Superhost
Home in Lawrenceburg
KY Bourbon Trail Lakefront - Year Round Hot Tub
Feb 12 – 19Individual Host,
€ 259 per night
4.81 out of 5 average rating, 124 reviews
Guest favorite
Home in Lewisburg
The Jolly Otter, Waterfront Getaway on Lake Malone
Apr 11 – 18Individual Host,
€ 121 per night
4.93 out of 5 average rating, 61 reviews
Guest favorite
Home in Lewisburg
The FunKY Bean
Dec 28 – Jan 4Individual Host,
€ 161 per night
4.92 out of 5 average rating, 38 reviews
Superhost
Home in New Concord
Cozy 2 bedroom KY Lake house * Beautiful Views! *
Nov 29 – Dec 6Individual Host,
€ 164 per night
4.71 out of 5 average rating, 65 reviews

Your guide to Kentucky

All About Kentucky

Bordered by the Ohio River to the north and the gently rolling Appalachian Mountains to the east, Kentucky is a land of rugged hills, raging rivers, endless caves, and oh so much good music. The state’s musical innovations span several genres, including bluegrass, blues, and country, spawned from the eastern hills where you can still find local artists and national acts performing in places like Covington, with its independent theaters and music venues. Along with being the birthplace of bourbon, Kentucky also boasts an impressive culinary tradition: its unique hickory smoked barbecue style has spread to the rest of the country and can be traced back to the Welsh settlers of the western wetlands.

For a dose of Kentucky culture, stroll Louisville’s fashionable Frankfort Avenue in with its trendy bars and bohemian vibes, or spend a day in the cute little town of Bardstown, where you can sample the state’s legendary distillate, see an outdoor musical, and visit a whiskey museum. If it’s the outdoors you crave, explore the rugged Daniel Boone National Forest or the sandstone bluffs in the Red River Gorge Geological Area that make up just a small portion of the almost 2 million acres of public land in the state.


The best time to stay in a vacation rental in Kentucky

Sitting between the warmer climate zone of the south and the colder northern areas of the country, Kentucky finds itself with generally mild temperatures and pleasant weather conditions throughout much of the year. Summers can bring high humidity, and with that often comes dramatic thunderstorms that sweep the landscape. For summer festivities, the famous Kentucky State Fair takes place towards the end of August, and the International Bar-B-Q Festival takes place around mid-May in Owensboro for a taste of the hickory smoked meats and spicy vinegar-based BBQ sauces the region is known for.

The diverse deciduous forests break out in a brilliant display of autumn hues during the fall, which can be a great time to search for cabin rentals in Kentucky, as the temperatures tend to be the mildest during the shoulder seasons. With the winter comes slightly lower temperatures and a reduction in humidity. Regardless of the time of year, the state's levels of rainfall tend to stay relatively stable.


Top things to do in Kentucky

Mammoth Cave National Park

Mammoth Cave National Park is a 52,830-acre limestone cave system in central western Kentucky with over 400 miles of surveyed tunnel, making it the most extensive known cave system on the planet. Spending as little as half an hour, or up to a full day of exploration, is possible in the underground passageways alone. Above ground, hiking, rock climbing, kayaking, and horseback riding are all on offer.

Berea

This rural countryside town is known as the Folk Arts & Crafts Capital of Kentucky. Artisans, artists, and creatives have flocked to this UNESCO Creative City for its tradition of supporting the arts since its earliest days as an English settlement. Museums and galleries like the Appalachian Artisan Center, where you can find exhibits, classes, and art for purchase, can be found in Berea’s old town Artisan Village alongside glass studios and other artisanal workshops for patronage.

Bluegrass Music Hall of Fame & Museum

Located in Owensboro, the Bluegrass Music Hall of Fame highlights the musicians and performers who helped bring the iconic style into the limelight. In addition, the museum has several displays and exhibits that detail the history behind the music, as well as lesson opportunities and several live concerts throughout the year.

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