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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!

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

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.

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!

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.

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

The Cabin/Fully Fenced for Pets/15 miles to RRG

Slightly off the beaten path our cabin is nestled on 2 acres of land with a fully fenced in yard making it perfect for all your furbabies. Start your day with coffee on the front porch in our rocking chairs. After a long day on the hiking trails come relax in our hot tub or sit by the fire pit out front. We are about 15 miles from Red River Gorge, less than 10 miles to Stanton and about 50 miles to Lexington. Need to escape from the world? This property is perfect for you!

Tiny Cabin At The Pond

Welcome to peace and quiet! If seclusion is what you're searching for, then you have found the place! Located on a hobby farm beside of a stocked fishing pond, it's as much of a destination as it is an accommodation. The closest neighbors are 3 friendly donkeys that love to greet guests at the fence for attention and ear rubs. Fishing poles and donkey treats are provided to round out your stay. We're 20 scenic minutes to Slade or Stanton and 25 to Mount Sterling.

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.