Vacation rentals in Owingsville

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Top-rated vacation rentals in Owingsville

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Guest favorite

Tiny home in Flemingsburg

4.96 out of 5 average rating, 139 reviews

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Jun 11 – 18

G$21,964 GYD per night

Guest favorite

Cottage in Wellington

4.95 out of 5 average rating, 123 reviews

The CliffTop Cottage by “Porch Swing Properties”

The Beautiful and Cozy CliffTop Cottage has a new Exterior look.. She looks beautiful. It’s the same Cozy Cottage sitting on the CliffTop above it all! With Breathtaking-views of rolling cliff tops surround you as you enjoy all that Mother Nature has to offer. Cozy and Serene 💕 Pool Table, Kayaks,Fish Cleaning Station,Lawn Games,Fireplace,Fire Pit,Bluetooth Speakers with Sound Bar Entertainment System. So much more! The most amazing views of the CliffTop with Sunsets that will warm your Soul.

Feb 16 – 23

G$28,308 GYD per night

Guest favorite

Home in Mount Sterling

4.96 out of 5 average rating, 139 reviews

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

Sep 15 – 22

G$16,734 GYD per night

Guest favorite

Home in Winchester

4.91 out of 5 average rating, 672 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Jun 12 – 19

G$12,770 GYD per night

Guest favorite

Guesthouse in Winchester

4.98 out of 5 average rating, 174 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We now have Wi-Fi!! Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

Dec 5 – 12

G$16,007 GYD per night

Guest favorite

Home in Salt Lick

5.0 out of 5 average rating, 40 reviews

Clear Creek Get Away

Located at the entrance of Cave Run Lake. Close to The Gorge, White sulphur atv& horse trails, Clear Creek lake ,hiking trails , Zilpo and leatherwood boat ramps all within minutes away. Natural bridge is only a 45 minute drive away and many other things to do close by also a short drive to the other side of cave run lake. This new tiny house has plenty of room inside and out. Sits along the Salt Lick Creek. Enjoy campfires in the evenings and relax

Feb 12 – 19

G$20,010 GYD per night

Guest favorite

Farm stay in Carlisle

4.99 out of 5 average rating, 121 reviews

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.

Jan 20 – 27

G$32,497 GYD per night

Guest favorite

Home in Flemingsburg

4.98 out of 5 average rating, 268 reviews

BLUE MOON LODGE- --UNWIND, CONNECT, REFUEL, RELAX!

If you are looking for a absolutely breathtaking, cozy place for just a few days break, or a complete unique, custom vacation for your family, you have found the place. Come and see for yourself what all the 5 star reviews are about. Every now and then you run across a place that just lifts a weight off your shoulders as soon as you open the door, THE BLUE MOON IS THAT PLACE!!!

Dec 16 – 23

G$25,743 GYD per night

Guest favorite

Cabin in Morehead

4.96 out of 5 average rating, 166 reviews

Morehead Cabin by the Lake

A relaxing space that can accommodate up to six people. This cabin is 3 min from Cave Run Lake and close to downtown Morehead and Morehead State University (15 min). Tucked up on a hillside surrounded by oak trees, enjoy the front porch and comfortable accommodations for the perfect, calming getaway. Great for work or play, this cabin has it all.

Oct 2 – 9

G$24,320 GYD per night

Guest favorite

Home in Stanton

4.93 out of 5 average rating, 142 reviews

Convenient & cozy home~walkable to grocery ~RRG

Conveniently located to some of the best spots Eastern Ky has to offer, and yet, The Towner still has the small town country charm that has come to be expected of the Red River Gorge area. Guaranteed clean and comfortable!! Property offers large storage building, with lock, for storage of bicycles, kayaks, hiking gear, etc.

Jul 17 – 24

G$20,852 GYD per night

Guest favorite

Cabin in Mount Sterling

4.96 out of 5 average rating, 202 reviews

The Honey Hut, Think of “ On Golden Pond"

The perfect honeymoon or family-friendly quality getaway spot, nestled in the quiet countryside of Mt. Sterling, KY - with a beautiful lake just steps from your back porch. Take your family or friends canoeing, paddle-boating, fishing. End your stay with a campfire in the fire pit to make this an unforgettable getaway.

Oct 22 – 29

G$36,562 GYD per night

Superhost

Cabin in Powell County

4.84 out of 5 average rating, 129 reviews

Elk Track Cabin near the RRG & Natural Bridge SP.

Elk Track Trail Cabin is your secluded get-a-way, a scenic 20-25 minute drive from Red River Gorge (approx. 10 miles) and Natural Bridge State Park (approx 14 miles). Situated off a picturesque drive through the blue grass hills, you'll feel cozy and comfortable, yet having the feel of camping out.

Mar 20 – 27

G$22,586 GYD per night