Holiday rentals in Cynthiana

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cynthiana

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

%{current} / %{total}1 / 1
Top Guest favourite
A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.
Home in Lexington
4.95 out of 5 average rating, 380 reviews

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.

Guest favourite
A spacious sleeping area includes a bed with a light-colored duvet, framed by large windows. A cozy seating area features a plush chair and small table, while an artwork with vibrant colors adds character to the wall. Warm wooden flooring enhances the inviting atmosphere.
Loft in Lexington
4.97 out of 5 average rating, 301 reviews

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!

Guest favourite
A living area features a comfortable gray sofa with accent pillows and an armchair, complemented by a wooden coffee table at the center. Natural light filters through a window covered with sheer curtains, highlighting the warm wooden flooring and neutral-colored walls.
Home in Cynthiana
4.97 out of 5 average rating, 33 reviews

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.

Top Guest favourite
A spacious living room features a large brown sofa adorned with decorative pillows and a cozy red recliner. A patterned area rug sits centrally, while wood paneling and beams create a rustic ambiance. Natural light floods in through large windows, illuminating the inviting space.
Cabin in Cynthiana
4.96 out of 5 average rating, 103 reviews

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.

Top Guest favourite
An outdoor area features a gravel patio surrounded by lush greenery. Two wooden benches face a fire pit, with additional seating provided by tasteful Adirondack chairs. A shaded umbrella sits above a small table near the cabin entrance, creating a welcoming space for relaxation.
Cabin in Sadieville
4.97 out of 5 average rating, 307 reviews

*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.

Guest favourite
Home in Cynthiana
5 out of 5 average rating, 22 reviews

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!

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, 897 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.
Guesthouse in Winchester
4.95 out of 5 average rating, 109 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
The exterior of a charming cabin is showcased, featuring a green metal roof and wooden porch. Bright sunflowers bloom in front of the cabin, while an American flag gently flutters. The sky is clear with a few fluffy white clouds.
Cabin in Cynthiana
4.98 out of 5 average rating, 130 reviews

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!

Guest favourite
The exterior entrance features a covered porch with two blue chairs and a small black table. A dark door with number 261 is framed by decorative light fixtures. Lush green bushes line the front, and a set of steps leads from the porch to the yard.
Home in Lexington
4.89 out of 5 average rating, 157 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 comfortable living area features a gray sofa facing a wooden coffee table. A recliner is positioned adjacent to the table, with a floor lamp providing soft light. A television is mounted above a white fireplace, and a vase of blue flowers adds a touch of color.
Apartment in Cynthiana
4.96 out of 5 average rating, 116 reviews

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.

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.

Popular amenities for Cynthiana holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Harrison County
  5. Cynthiana