Holiday rentals in Sharpsburg

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Top-rated holiday rentals in Sharpsburg

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Top guest favourite
A wooden sign reading 'LENMAR FARM Est. 2019' is prominently displayed on a green metal gate. The sign showcases a natural wood grain, and the background features an open field with scattered trees and horse jumps.
Farm stay in Winchester
4.93 out of 5 average rating, 172 reviews

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Guest favourite
A wide outdoor porch features several black chairs adorned with floral cushions. Potted plants are positioned around the area, contributing to a lush environment. The space is partially shaded, offering a relaxed setting for outdoor enjoyment.
Flat in Carlisle
4.9 out of 5 average rating, 112 reviews

Modern Trailer Living

Freshly painted, updated and fully furnished, towels, tp/pt, most kitchen utensils, microwave, coffee pot/press, full size stove and fridge, TV in living room, wi-if when accessible must hv ur own streaming device, outdoor porch with smoking Ok!! This is a non smoking space!!!! No Smoking/vaping in unit, if you do a charge will be imposed!!!! No exceptions!! if you’re not a registered guest here you must park outside the gate which remains closed/opened but remains closed otherwise!

Top guest favourite
The cottage's exterior is characterized by a welcoming porch featuring rocking chairs and a bench. Black star accents adorn the light-colored siding, framed by green grass and trees. Large windows invite natural light, enhancing the view of the surrounding fields.
Home in Morehead
5 out of 5 average rating, 113 reviews

Sunset Cottage

Sunset Cottage is located among the farms and fields of Morehead, KY. Conveniently situated off of I-64, within 10 min. of Cave Run Lake, App Harvest, Ind. Stave Co., and MSU. This newly remodeled 2-bedroom home has 1 queen, 1 full, & 1 twin bed. A quaint living room with an elec. fireplace, full kitchen, dining area, washer/dryer & an outdoor space that includes a gas grill and fire pit. There is plenty of room to park your boat and a porch to relax and enjoy the beautiful sunset

Guest favourite
A comfortable living area features a light gray sofa adorned with decorative pillows. A patterned armchair sits adjacent to the sofa. A wooden coffee table is centered on a soft area rug, while natural light enters through two windows, brightening the space.
Flat in Lexington
4.88 out of 5 average rating, 132 reviews

Hidden Gem|One Bedroom Apt Downtown Lexington

Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

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
4.91 out of 5 average rating, 890 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 well-lit sleeping area features a spacious bed draped in a white coverlet, flanked by two small windows with light blue trim. A blue chair adds a pop of color, while a wooden table is set with cups and a coffee maker, enhancing the inviting space.
Guest house in Winchester
4.96 out of 5 average rating, 106 reviews

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.

Guest favourite
A colorful logo features a cartoon chicken wearing sunglasses and giving a thumbs-up, set against a smooth blue background. The stylized letters 'WR' appear prominently in blue, while the chicken forms a friendly and inviting character.
Farm stay in Winchester
4.82 out of 5 average rating, 144 reviews

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Guest favourite
A modern kitchen is equipped with stainless steel appliances and sleek countertops featuring a marble pattern. Bar stools provide seating at a breakfast bar, while a flat-screen television is mounted on the wall. Natural light illuminates the space, enhancing the open layout.
Home in Lexington
4.88 out of 5 average rating, 153 reviews

Luxurious 1-bedroom with free parking on premise

Historical home located in the heart of Lexington, Kentucky. Few minute walk to Woodland Park, Kroger, Starbucks, bars, and restaurants. Gas station right around the corner. A convenient 3 minute drive and you're in the middle of downtown Lexington. Rupp Arena (1 mi), Kroger Field (1.5 mi), Keeneland (7 mi), Kentucky Horse Park (10 mi), Buffalo Trace Distillery (26 mi). 1GB fiber optic wifi. (This home is a duplex.)

Guest favourite
A spacious bedroom is highlighted by a comfortable bed with a sleek black headboard. Soft lighting from bedside lamps creates a warm ambiance. Light-colored bedding contrasts with the room's gray walls, while a window allows natural light to fill the space.
Home in Stanton
4.88 out of 5 average rating, 193 reviews

RRG Climbers Choice Stay-Wifi- No cleaning fee

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. Fully furnished duplex (SIDE B) is minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, The Gorge Underground, Callie's Lake, La Cabana & Kroger. On the Scenic Byway in Stanton. Side A & B can be booked together if availability allows.

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, 170 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.

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, 343 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!!!

Top guest favourite
A charming farmhouse is visible with a red metal roof and a welcoming porch featuring wooden rocking chairs. Brightly colored mums are arranged in front, while chickens roam freely in the grassy area, contributing to the rural atmosphere.
Home in Paris
4.94 out of 5 average rating, 201 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).

Popular amenities for Sharpsburg holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Bath County
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