Holiday rentals in Cynthiana

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

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.

Authentic Hilltop Log Cabin, 360° Views, Sleeps 15

Rustic Appalachian log cabin located in the countryside of Cynthiana, Ky. Come experience the serenity of the sunrise from the wrap-around porch while sipping your coffee in an Amish-built glider chair. Situated on 25 rolling acres, scenic views can be taken in from all sides. Fishing is available from a stocked pond where deer come to drink in the evening. The cabin sleeps 15 comfortably or 2 for a romantic retreat. Turn off the beaten path and experience the tranquility of the country.

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

Sunrise Acres

Cozy escape nestled on 6 acres of picturesque countryside. with a charming 1-bedroom loft (5'5" clearance) featuring a comfy queen bed. Unwind on the back deck with stunning sunset views, relax in hammocks, or gather around the fire pit. Full kitchen, one bathroom, and entertainment galore with two TVs, a dvd player with a variety of movies, a Pac-Man arcade game, and board games. Lounge on the plush 12 ft feather-down sectional or enjoy the front porch. Perfect for a relaxing getaway!

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.

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.

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!

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.)

Cozy & Private Apartment in the Heart of Cynthiana

Enjoy everything Cynthiana has to offer at your fingertips! In the center of historic downtown Cynthiana, this space will place you walking distance from multiple eateries, a coffee shop, several boutiques, an antique store, gift shops, and a brewery across the street. You will also be a few steps away from one of the most haunted places in America, Roh's Opera House; one of the oldest theaters in the U.S.

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.