Holiday rentals in Sharpsburg

Haymark Farmhouse: cozy & clean, with outdoor fun!

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 sitting area and table for eight. Explore our 275 acre farm! Pet our cute farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ... If you need room for more folks, check out Thomas Road House.

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Near to EKU; discounts to 10%

Located 5 minutes from I-75. Newly renovated basement apartment perfect for solo travelers, friends or couples and is pet friendly. Take it easy at this country setting and enjoy the pool. Convenient to EKU, stay after a day at Keeneland, exploring the Bourbon Trial, concerts or just a peaceful and relaxing getaway. Available small hot tub on request. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

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!

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.

The Cedar Shack

Enjoy Cave Run Lake or take a short drive (21ish miles) to Red River Gorge from our Tiny Cabin. Our Cedar Shack is a 12ft x 28ft with a 4ft porch, equipped with dual rocking chairs. The Cedar Shack is appropriately named as it is finished fully is cedar from floor to ceiling. Pets are welcome in most instances but they must be included in the guest list and there is a fee. No exceptions.

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.