Holiday houses in Cynthiana

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Top-rated holiday rentals in Cynthiana

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

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Guest favourite
A bedroom features a four-poster bed with decorative pillows and a patterned bedspread. A small table and an armchair are positioned near a window adorned with floral curtains. Lamps provide soft lighting, and a mirror reflects the room's inviting tones. Hardwood floors are complemented by an ornate area rug.
Apartment in Cynthiana
5 out of 5 average rating, 17 reviews

Formal & Friendly, 2nd Fl., 113 N. Main #3, c 1811

You’ll find luxury and style in this unique space. Enjoy the 2nd floor of a brick rowhouse built in 1811. It’s old, but has modern amenities. Search “Wesley Roberts House” on the National Register of Historic Places. You are in downtown Cynthiana, pop. 7,000 with, about a block away, restaurants, shops and a real movie theater. 35 minutes from Lexington, 20 from Georgetown, 60 to Cincinnati. Some Main Street traffic noise, but not bad. Fiber optic Wi-Fi, 55” TV. Off-street parking, central HVAC.

Top Guest favourite
The front porch features wooden decking with a railing, providing a welcoming entrance. Multiple chairs are arranged along the porch, with a door leading into the cabin. The surrounding landscape includes trees and gravel, enhancing the rural farm setting.
Home in Sadieville
4.99 out of 5 average rating, 145 reviews

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.

Top Guest favourite
A view from a welcoming porch is presented, featuring a table and chairs. Through the open doorway, a vibrant sunset is visible, casting warm hues across the sky and illuminating the countryside landscape with trees in the background.
Home in Falmouth
4.99 out of 5 average rating, 129 reviews

Countryside Inn (9 mi to Ark)| Fire Pit|Barn Games

You won’t forget the peaceful surroundings of this country charm destination. The Countryside Inn is located on a beautiful rolling ridge with amazing countryside sunrises and sunsets. During your stay you will experience the FUN rustic living with all the comforts of home. Come experience this simple country living. Far enough out to enjoy the country but close enough to visit many Attractions. The Ark Encounter is only 9 mi. away. With many other attractions within 30 min. to an hour!

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, 305 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.

Top Guest favourite
A charming cottage exterior is framed by lush greenery and mature trees. The light gray siding is complemented by white columns at the entrance. A brick walkway leads to the front door, bordered by neatly manicured bushes and seasonal flowers.
Home in Georgetown
4.98 out of 5 average rating, 114 reviews

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

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, 883 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.

Guest favourite
A welcoming duplex structure features a traditional design with a high-pitched roof. Each suite has a separate entrance, framed by porches. Lush green grass surrounds the home, with scenic views of the expansive landscape visible in the background.
Farm stay in Cynthiana
4.93 out of 5 average rating, 87 reviews

Sultan's Hideaway @ Stillwater Farm & Arena

Escape to serenity in our easily accessible suites/ duplex 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.

Top Guest favourite
A charming one-bedroom house presents a welcoming facade, featuring a large wrap-around porch. Comfortable outdoor furniture is arranged on the porch, and surrounding greenery enhances the tranquil country setting. A pathway leads to the entrance, inviting guests to explore the beautiful outdoor space.
Bungalow in Dry Ridge
4.98 out of 5 average rating, 775 reviews

The Cute Little House Near The Ark Encounter

The "Little House" is a cute 1 bedroom house located on our farm in a beautiful country setting with 6 acres of outdoor space for relaxing. It is separate from our home and is all yours. It is conveniently located only 8 miles from the Ark Encounter and you only need to make one turn to get there. We have chickens, ducks, turkeys, a horse, and 11 goats. We also have a 1/2 mile nature trail to explore with a scavenger hunt, and a campfire spot with free firewood.

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, 128 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 living area is designed with comfortable seating, including a spacious sofa and patterned armchairs. A wooden coffee table sits in the center, and a TV is positioned on a console table. Natural light enters through large windows, providing a bright ambiance.
Apartment in Hill N Dale
4.94 out of 5 average rating, 180 reviews

One Bedroom Apt - Close to Everything

This apartment is the perfect location for catching a UK game, a weekend at Keeneland, business trips or clinical rotations. It features an open concept kitchen and living area. The bedroom connects to a master bath with beautiful counter tops and fixtures. Simply pull the barn doors shut for privacy from the living area. Also features new stainless steel appliances, granite countertops, cultured marble shower, washer/dryer, and convenient parking.

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

When is the best time to visit Cynthiana?

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Quick stats about holiday rentals in Cynthiana

  • Total holiday rentals

    Explore 20 holiday rentals in Cynthiana

  • Nightly prices starting at

    Cynthiana holiday rentals start at $122 NZD per night before taxes and fees

  • Verified guest reviews

    Over 650 verified reviews to help you choose

  • Wi-Fi availability

    20 of Cynthiana holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cynthiana rentals

  • 5 Average rating

    Cynthiana stays are highly rated by guests—averaging 5 out of 5!

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