Vacation rentals in Owingsville

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Top-rated vacation rentals in Owingsville

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Top guest favorite

Apartment in Mount Sterling

4.96 out of 5 average rating, 77 reviews

Historic 2-Bedroom Apartment in Downtown

Charming apartment in the historic Farmers National Bank building in downtown Mount Sterling. Recently renovated, the apartment provides the comfort and amenities of home, yet retains all of the character of the original building. Within walking distance of many great restaurants and if you’re in the mood to shop, stop in to Lily Aesthetics downstairs or take a stroll down Main Street to find a variety of great shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

Superhost

Home in Mount Sterling

4.84 out of 5 average rating, 213 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!

Superhost

Cabin in Frenchburg

4.9 out of 5 average rating, 186 reviews

Modern Woodland Cabin w/Hot Tub

The perfect place to escape and wake up amongst trees or spend a weekend w/friends! Welcome to Tall Stüga - "Pine Cabin". Our incredibly modern, Scandinavian-themed cabin! You're located on the Sheltowee Trace, minutes from Cave Run Lake and only 25 country miles from Red River Gorge. :) There is public access to hiking trails, boat docks, horse camps, local golf course, parks & more. Plus, you'll be close to numerous quaint little towns, state forests, antique stores & local markets.

Top guest favorite

Home in Wellington

4.99 out of 5 average rating, 114 reviews

Luxury Cliffside Hammock House

Escape to a modern luxury hammock oasis: with cozy indoor & outdoor loft-net hammocks, memory foam beds with MyPillow pillows for supreme comfort, and MyPillow towels enhancing the spa-like bathrooms featuring rainfall showers and body jets. Adventure awaits with a private trail into Daniel Boone National Forest, a hot tub, and a pool table. This space isn't just a stay but an experience, designed for those seeking luxury, comfort, and a touch of adventure. Not Suitable for children.

Top guest favorite

Home in Mount Sterling

5 out of 5 average rating, 83 reviews

High Street Hideaway home atmosphere for relaxing

High Street Hideaway, relax away from the city in a spacious well appointed home atmosphere. Large back deck for relaxing and dining. No need to park on the street and walk a flight of stairs! Private parking with 4-5 steps up to deck and back door! *Access to Lexington 30-45 minutes away via Interstate 64. * 45 minute drive to the natural beauty of Red River Gorge for hiking/ climbing *30 min to Cave Run Lake * Three blocks to local shops, eateries, and town festivals!

Top guest favorite

Home in Winchester

4.91 out of 5 average rating, 830 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 non-gentrified 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.

Superhost

Farm stay in Winchester

4.8 out of 5 average rating, 128 reviews

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Top guest favorite

Home in Salt Lick

5 out of 5 average rating, 62 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

Guest favorite

Tiny home in Salt Lick

4.89 out of 5 average rating, 9 reviews

8 Cottage at Cave Run

Kick back and relax at this cozy tiny home! We are located within minutes to Cave Run Lake and less than 15 minutes to downtown Morehead, Kentucky. A different variety of restaurants, including Pop's BBQ, Elliot's Pizza, Los Tres Agaves, Frosty Freeze, and more. Interested in kayak and boat rentals, the spillway, the fish hatchery, and more? This is the perfect opportunity to stay and enjoy these activities!

Guest favorite

Cabin in Salt Lick

4.91 out of 5 average rating, 149 reviews

The Cedar Shack

Enjoy Cave Run Lake or take a short drive (21ish miles) to Red River Gorge from our Tiny Cabin. Our Cedar Shack is a 12ft x 28ft with a 4ft porch, equipped with dual rocking chairs. The Cedar Shack is appropriately named as it is finished fully is cedar from floor to ceiling. Pets are welcome in most instances but they must be included in the guest list and there is a fee. No exceptions.

Guest favorite

Farm stay in Carlisle

4.99 out of 5 average rating, 160 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.

Top guest favorite

Home in Flemingsburg

4.98 out of 5 average rating, 331 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!!!