Vacation rentals in Mount Sterling

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.

Stylish Studio in Mt. Sterling – 7 night min

Experience comfort and convenience in the heart of Mt. Sterling with this modern downtown studio! This designed space includes everything you need for a month-long stay —a kitchen, cozy sleeping area, private bathroom, and access to essential amenities such as high-speed WiFi, smart TV, and on-site laundry. Our Mt Sterling stay is ideal for corporate relocation, extended work engagements, vacationing in Mt Sterling KY, and other short or long-term lodging needs, offering a calm, stylish space.

Stylish Loft 2Bdrm Winchester ky near Lexington

New York style loft meets historic renovation—Central Kentucky. Meet charming Winchester. Under hr. to Keeneland race track, Kentucky Horse Park, & the spectacular Red River Gorge/Natural Bridge. Lexington 30 min. Paris, Georgetown, Richmond & Berea close too. Many local, small businesses-restaurants, brewery, distillery, shops, antiques, flea markets, & historical sites! Unit is on the second floor—may not be right for all abilities. Public, street parking. See our lovely town renovation.

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.

The Towner

Escape to The Towner—your perfect home base for Red River Gorge adventures. Enjoy the rare combination of small-town convenience and easy access to Kentucky’s top outdoor destinations. Walk to restaurants, shops, and groceries, then spend your days hiking, climbing, kayaking, zip-lining, and exploring the Gorge just minutes away. Thoughtfully appointed with high-speed WiFi and all the comforts of home, The Towner is ideal for couples, families, and extended stays alike. ✨🏡🌄

Pawplex

✨ Modern Pet-Friendly Retreat – Right Next Door to the Dog Park! ✨ This stylish, fully renovated 1-bedroom studio is designed for comfort, accessibility, and furry friends. You’ll love falling asleep to the soft hum of downtown while knowing your pup has their own cozy crate and the best dog park in town just outside the door. Come experience downtown living that’s stylish, accessible, and truly dog-approved! We can’t wait to host you and your four-legged best friend! 🐾

Carriage House Gardenside

Privacy and Convenience are yours when you stay at the Carriage House Gardenside. Located in historic Winchester, Carriage House Gardenside offers easy access to Lexington, the Kentucky Horse Park, Keeneland Race Course, the Bourbon Trail and Red River Gorge. Situated across from College Park and steps away from Winchester's public gym (indoor swimming pool and fitness center). Space features a king sized bed, large TV, coffee bar, devoted work space and full bath.

Seclusion Cabin - Tower, Treehouse, Koi Pond

Seclusion is a completely custom, hand-crafted cabin complete with a treehouse room, koi pond, rocky landscape, observatory tower and more in an unbeatable location. This cabin is located just a mile or two off the Slade, KY exit on top of a ridge in Red River Gorge. Built by Paul Rhodes in his spare time, this passion project took over six years to complete and boasts a uniqueness unrivaled by other accommodations.

Larkspur Cabin with Hot Tub near Red River Gorge

Located on the edge of Red River Gorge Geological Area in 20 acres of peaceful woodland and rolling hills, our property has the perfect blend of accessibility and seclusion. Enjoy birds at the porch feeders, and all the flowers blooming in the garden in the summer . Enjoy the hot tub! It's just 15 minutes from the Red River Gorge and Natural Bridge State Park and 5 minutes from Stanton for shops and restaurants.

Five O’clock Somewhere

A brand new studio home w luxury king bed, tile shower In full bathroom, and kitchen! Located in downtown Mt. Sterling! WiFi Smart TV Coffee maker Fridge Microwave Hot plate 5 minute walk to downtown Mount Sterling ! 4 minutes from I-64 exit Bring your pet and stay with us! This is a brand new home, yard still needs seed and straw and 14 steps to get into home out front! On street parking

Peaceful Kentucky Ranch

Unplug and unwind at our peaceful 40-acre Kentucky ranch. This spacious 3BR, 2.5BA home offers views of Texas Longhorns and alpacas, plus modern comforts in a serene country setting. Relax on the porch, gather by the fire pit, and explore nearby attractions like Buffalo Trace Distillery, Kentucky Horse Park, hiking trails, and golf. Perfect for families, couples, or Bourbon Trail adventurers.