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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.

Short drive to RRGorge, walk to food & shopping!

Cozy home just 10 minutes to Red River Gorge, one minute from Mountain Parkway, with the convenience of restaurants and shopping just steps from the front porch! Updated and spotless! Private and cozy back yard with fire pit, Adirondack chairs, charcoal grill, and picnic table for making fun evenings at home! Chinese food across the street and Kroger steps away from porch! Just a 3 minute walk to several restaurants! Relax and enjoy family night with games and cards after your hike!

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.

Maple Grove at Red River Gorge/Hot tub/Arcade!

Escape to our 8+ acre retreat featuring a remodeled 3000 sq ft home with 5 bedrooms and 3 baths, accommodating up to 10 guests. Indulge in a gourmet kitchen, leather furniture, private hot tub, and arcade room. Stay connected with 300mb internet and Roku streaming. Outdoor amenities include EV charging, firewood, basketball, cornhole, and kids’ bikes. Relax in the ‘hammock hideaway’ or on the covered porches. Where we ensure your stay is unforgettable, prioritizing comfort and relaxation.

Firethorn’s Hilltop Haven

Country living at its finest. The home is nestled on a 140 acre seasonal working farm with lush open fields in scenic rural but Central Kentucky. This peaceful getaway gives a glimpse of what life on the farm and being in nature is like. Surrounded by open rolling fields, the perfect place to relax, take a walk, take a dip in the pool, or just be in nature. This home has it all. Family friendly. Pool available from May 19th to September 9th. Rates apply. Can park RV's & trailers.

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm 5 minutes to DT Winchester Lexington 20min. Easy access 5min. I64; 15min. I75 / I64 Discounts Weekdays in July Centrally located: Eateries & Historical Sites Lexington 20min State Parks Meadow Green Music Park 20min Keeneland 30.4mi. Kentucky Horse Park 30min Red River Gorge 35min Ark Encounter 45min Creation Museum 1hr 30min ~Home is surrounded by our family farm beginning of Scenic Rt.15 *All guests must be registered to see price of your stay before booking

Rustic Mt. Sterling Cabin2 Near Downtown • Pets OK

Rustic Mt. Sterling Cabin 2 Near Downtown • Pets OK ★☆ ABOUT THIS SPACE ☆★ Tucked away in the rolling hills of Mt. Sterling, this rustic cabin offers the perfect blend of country charm and modern comfort. Just a short drive from the historic downtown district, you’ll have easy access to local shops, dining, and small-town charm—then come home to peace and quiet. Inside, unwind with a movie on the 55" smart TV, play a round of cards, or cook up something hearty in the fully equippe

Pauline's Paradise

Welcome to Pauline's Paradise! You can enjoy a quiet and relaxing stay in our 2 bedroom home, with an adjustable King bed in one and twin beds in the other. You'll find a full kitchen, washer/dryer, wifi and Roku TV. We welcome well behaved pets. Handicapped entrance ramp. We're 25 min. away from Natural Bridge, Sky Bridge, Red River Gorge, hiking, underground kayaking and more. We're less than an hour from Lexington. We ask that you refrain from smoking inside during your stay.

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.

Horse & Flower Farm Barn Loft

Enjoy peace and quiet in the countryside surrounded by Stoner Creek. Old Bridge Farm is a horse farm and also the home of Blooms of Bourbon County which is a flower, fruit and vegetable grower utilizing organic growing practices. Our 100 year old tobacco barn has been converted into a stable with a large rustic loft above with all of the conveniences of home. We're off the beaten path on a very quiet road in the middle of horse country. Come...relax, escape, recharge.

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.