Holiday houses in Cynthiana

80 acre farm/beautiful views/donkeys & goats

Cannon Farm is a 80acres working farm that has plenty of trails, 1 pond, and a creek that runs through it. Your cabin is a new 2 bedroom, 1 bath that can accommodate up to 5 people. Relax and enjoy the sunrise on your big front porch or have a fire and BBQ on your back patio. We are 15 minutes from the very cute town of Cynthiana and only 30-40 minutes away from Georgetown and Lexington. Just a short drive to many attractions like Kentucky Horse Park, Ark Encounter and all the bourbon tours.

Rustic Container Cabin • Farm Stay • Near Ark

Discover the charm of our rustic container cabin on a wooded ridge of our family farm. Freshly painted exterior—same comfy interior. 30 min to Ark Encounter. Unwind on the sunset porch under string lights, enjoy the fire pit & grill, and breathe crisp Kentucky air as you explore 200 acres of hills and trails. Inside: vintage farm touches, comfy memory-foam bed(s), efficient kitchenette, heat/AC, and a one-of-a-kind bath. A peaceful base for the Ark and Boutbon Trail. A true Kentucky farm stay.

Too Comfy / Too Cozy Home in Cyn

Enjoy a stylish experience close to local wedding venues. This unit was newly built in the Summer of 2024. No stairs provides easy access to the unit. New furnishing offers you a comfortable stay for you or for a family. Bright and cheery decor incorporates some of the "new" Cynthiana with the history of this charming small town. Just a few minutes from industry such as Bullard, 3M, and E-Z Pack Holdings. Close to the downtown area, restaurants, Harrison Memorial Hospital, and local events.

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!

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

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.

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.

Duchess's Retreat at Stillwater Farm & Arena

Escape to serenity in our easily accessible suites that feature a kitchenette, Smart TV, bathroom, large front porch, and scenic views all with access to a washer and dryer. Conveniently situated halfway between Cincinnati and Lexington, it's a short drive to the Kentucky Horse Park and the Ark Encounter—both just 35 minutes away. Experience rustic charm and modern comfort in this rural retreat. Trailer parking, horse boarding and access to indoor arena available.

Quittin' Time - Country Cabin at Hickory Holler

Come visit the beautiful countryside and stay in this adorable cabin right outside the city limits of Cynthiana, KY! Located on over 90 acres, this place has a million dollar view of a large pond and huge pasture fields. It's only a short 5 mile drive into town where there is an abundance of local restaurants and small downtown shops. Enjoy a campfire with the on-site fire pit or go for walk and do some exploring. Come enjoy a very peaceful and quiet getaway!