Holiday rentals in Sharpsburg

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.

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!

Haymark Farmhouse: cozy, country memories

Welcome to Haymark Farmhouse, built in 1907. Relax in front of the fireplace with electric logs, play games (provided), and cook in the well-supplied kitchen or on the gas grill out back. Enjoy the outdoor fire pit (wood provided) and the lighted outdoor patio area and table for eight. Explore our 275 acre farm! Check out our farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ...Enjoy your time at Haymark Farm.

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.

Maple Point - Dream Cabin in RRG

Welcome to Maple Point, an immaculate 1 bedroom + 1 bath cabin located in the heart of Red River Gorge. Completed in 2024, this property was thoughtfully created by a builder and designer to provide guests with a comfortable and memorable space to enjoy this region of Kentucky. Whether you are looking for a central base from which to explore, a quiet getaway where you can relax, or an inspiring space to work, we would love to have you come stay.

Modern Cabin • Private Hot Tub • Fire Pit • RRG

“Imagine an Ikea showroom with a beautiful wall of windows looking out into the woods” — Maggie ⭐️⭐️⭐️⭐️⭐️ Escape to The Outpost, a design-forward cabin tucked into six wooded acres in the foothills of Red River Gorge, within the Daniel Boone National Forest. Floor-to-ceiling windows frame the woods, while high ceilings and an open layout keep this cozy hideaway bright, calm, and connected to nature.

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.

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.

Slow Motion Hideaway Cave Run Lake/RRG - hot tub!

Breathe deep. Slow down. Stay awhile. Slow Motion Hideaway is a cozy A-frame cabin tucked in Kentucky’s Daniel Boone National Forest, just minutes from Cave Run Lake and close to Red River Gorge. Hike, kayak, ride ATVs, or spend the day on the water—or curl up with a good book and never leave the cabin. A quiet place to reconnect—with the woods, with your people, or with yourself.

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!!!

Hygge Nock at Lush Hollow

Nestled perfectly on a ridge of our 40-acre property, minutes from Cave Run Lake and 25 miles from Red River Gorge, this Scandinavian-themed cabin is the perfect ridge-top retreat. Enjoy nearby hiking, boating, and golfing. Relax with a hot tub, pellet grill, and cozy fire pits. Explore quaint towns, state forests, and local markets. Your ideal super cozy, secluded getaway awaits!