
Holiday rentals in Sharpsburg
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Top-rated holiday rentals in Sharpsburg
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Robbie’s Rest: Amazing Mountaintop Sunrises
2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible
4.98 out of 5 average rating, 380 reviews
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.
4.97 out of 5 average rating, 31 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.
4.99 out of 5 average rating, 173 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!
5.0 out of 5 average rating, 115 reviews
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.
4.99 out of 5 average rating, 361 reviews
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.
4.99 out of 5 average rating, 199 reviews
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.
4.96 out of 5 average rating, 101 reviews
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.
4.95 out of 5 average rating, 408 reviews
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.
5.0 out of 5 average rating, 23 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.
4.99 out of 5 average rating, 180 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!!!
4.98 out of 5 average rating, 365 reviews
Stoner View Farm
Hello! Our place is close to Paris, Mt. Sterling, Winchester and Lexington. . You’ll love our place because of its scenic views, privacy and seclusion. It sits on a 10 acre farm back off a country road that backs up to Stoner Creek! Our place is good for couples, solo adventurers, business travelers, and families (with kids).
4.94 out of 5 average rating, 208 reviewsPopular amenities for Sharpsburg holiday rentals
Other great holiday rentals in Sharpsburg

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
4.97 out of 5 average rating, 31 reviews
The Boarding House | Circa 1812 | Ideal Location
5.0 out of 5 average rating, 6 reviews
Stylish Studio in Mt. Sterling – 7 night min
5.0 out of 5 average rating, 7 reviews
Five O’clock Somewhere
4.88 out of 5 average rating, 40 reviews
The Nest at Lush Hollow
4.97 out of 5 average rating, 78 reviews
The Lodge at Marble Creek
4.98 out of 5 average rating, 54 reviews
The Cottage at Stillhouse Cabin
4.96 out of 5 average rating, 57 reviews
Red Bird Estates
5.0 out of 5 average rating, 71 reviewsDestinations to explore
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- Ark Encounter
- Kentucky Horse Park
- Carter Caves State Resort Park
- Rupp Arena
- University of Kentucky
- Castle & Key Distillery
- The Arboretum, State Botanical Garden of Kentucky
- Raven Run Nature Sanctuary
- McConnell Springs Park
- Kroger Field
- Talon Winery & Vineyards
- Equus Run Vineyards
- Masterson Station Park
- Fort Boonesborough State Park





