Holiday houses in Sharpsburg

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Top-rated holiday rentals in Sharpsburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Irvine
4.98 out of 5 average rating, 111 reviews

Premium A-Frame Retreat | Hot Tub, Sauna & Pond

Escape to a peaceful A-Frame retreat in Irvine, KY, where valley views, thoughtful comforts, and private outdoor spaces invite you to slow down and reconnect. ✓ Hot tub under the stars ✓ Infrared sauna + private gym ✓ Fire pit, pool table, and ping pong ✓ Private pond, pedal boat + catch-and-release fishing ✓ Day trips to Nada Tunnel, Red River Gorge & Berea Pinnacles ✓ Great for couples, families & small groups Sleeps 7; space for 8 upon approval. No TV by design—to slow down and reconnect.

Top Guest favourite
A charming two-story country home is set on a gently sloping lawn, featuring a red front door and several windows that allow natural light. Green shrubs and grass surround the entrance, complemented by a clear blue sky overhead.
Home in Sharpsburg
5 out of 5 average rating, 20 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.

Top Guest favourite
A modern black house is set on a rocky landscape, surrounded by lush greenery. A wooden post carved with bear figures adds natural charm. Large windows invite light into the home, enhancing the connection between indoor and outdoor spaces.
Cabin in Wellington
4.99 out of 5 average rating, 158 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.

Top Guest favourite
A hot tub is positioned on a covered deck, overlooking lush green hills and treetops. The water is bubbling, inviting relaxation while the natural landscape offers a serene backdrop. Sunlight filters through the trees, creating a peaceful ambiance.
Cabin in Frenchburg
5 out of 5 average rating, 119 reviews

The Bluff on Amos Amazing Views!

This unique place has a style all its own. Centrally located between Red River Gorge and Cave Run Lake. Enjoy a hike at the gorge or a day at the lake. Come back enjoy soaking in the hot tub and take in the views!!! This spacious one bedroom one bath with tub/ shower is the perfect place for a getaway. It is equipped with full size appliances and everything you need to prepare a meal. The outdoor fire pit and charcoal grill are perfect for any outdoor cooking and relaxing!!!

Top Guest favourite
The kitchen features a large central island with a dark finish, complemented by light granite countertops. Bright, white cabinetry surrounds the space, enhanced by overhead pendant lighting. Stainless steel appliances, including a refrigerator and microwave, provide modern convenience amid an open layout.
Home in Mount Sterling
5 out of 5 average rating, 107 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!

Top Guest favourite
The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.
Home in Winchester
4.92 out of 5 average rating, 929 reviews

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.

Top Guest favourite
A spacious outdoor deck features a hot tub and a fire table surrounded by comfortable chairs. Large windows frame serene views of the surrounding forested hills, inviting relaxation in a tranquil setting.
Cabin in Pine Ridge
4.98 out of 5 average rating, 333 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.

Guest favourite
A modern Scandinavian-style cabin features a black exterior and large windows. A spacious deck is attached, offering outdoor seating and a fire pit. The surrounding landscape showcases lush greenery and distant hills, creating a serene atmosphere for relaxation.
Cabin in Frenchburg
4.91 out of 5 average rating, 234 reviews

Tall Stüga at Lush Hollow

Welcome to Tall Stüga! Our incredibly modern, Scandinavian-themed cabin! You're located on the Sheltowee Trace, minutes from Cave Run Lake and only 25 country miles from Red River Gorge making it the perfect place to escape and wake up amongst trees or spend a weekend w/friends! There is public access to hiking trails, boat docks, horse camps, local golf course, parks & more. Plus, you'll be close to numerous quaint little towns, state forests, antique stores & local markets.

Top Guest favourite
Farm stay in Ewing
4.99 out of 5 average rating, 189 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.

Top Guest favourite
The cabin exterior showcases a wooden structure with large glass windows, allowing natural light to illuminate the interior. Surrounding foliage enhances the secluded feel, while a wooden deck extends from the entrance, leading to an outdoor space with a hot tub visible nearby.
Cabin in Stanton
4.95 out of 5 average rating, 391 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.

Top Guest favourite
A welcoming living space features hardwood flooring and soft gray walls. A comfortable sofa and patterned armchairs are arranged around a rustic coffee table. Ceiling fans provide ventilation, while large glass doors open to a view of the expansive yard.
Farm stay in Carlisle
4.99 out of 5 average rating, 173 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.

Top Guest favourite
A charming house is visible from a distance, featuring a welcoming porch supported by wooden railings. Lush greenery and bright yellow flowers create a vibrant landscape, enhancing the exterior. The house is complemented by a backdrop of trees, adding to the inviting atmosphere.
Home in Flemingsburg
4.98 out of 5 average rating, 353 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!!!

Popular amenities for Sharpsburg holiday rentals

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  2. United States
  3. Kentucky
  4. Bath County
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