House vacation rentals in Woodford County

5 out of 5 average rating, 26 reviews

Home in Midway

Stylish & Tranquil ~ Hot Tub ~ Jukebox ~ Mini-Golf

Step into the stylish and bright 3BR 1BA one-acre oasis in the heart of the picturesque bourbon country. It promises a relaxing retreat just a few minutes from local distilleries, scenic countryside landmarks, and exciting attractions. The modern design and a rich amenity list will leave you in awe. ✔ 3 Comfortable Bedrooms ✔ Bright Living Area ✔ Full Kitchen ✔ 9-hole Duck Duct Putt-Putt Golf Course ✔ Vintage Jukebox ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking See more below!

4.99 out of 5 average rating, 70 reviews

A charming cottage is set on two acres of land, featuring a wooden deck with steps leading to the entrance. A fire pit and several outdoor seating options are visible in the grassy area. Lush trees surround the property, enhancing the natural setting.

Home in Lawrenceburg

Bourbon Barrel Cottages #4 on the Kentucky Bourbon Trail

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish cottage in the center of Kentucky’s Bourbon Country. Enjoy wildlife and nature in one of our 5 two bedroom cottages. Each sits on two acres. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 min from anything! Sit out on your deck or at your own private fire pit at night and listen to the sounds of birds, frogs and other wildlife. **There will be a $500 for smoking inside of the cottage**

4.9 out of 5 average rating, 111 reviews

A charming retreat features a stone chimney and a covered patio area with seating, set against a backdrop of mature trees. A stack of firewood is neatly arranged beside the building, while fallen leaves blanket the ground, indicating a serene outdoor space.

Home in Kentucky

The Stagg House on the Ky River

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

4.99 out of 5 average rating, 121 reviews

A charming cottage exterior is framed by a large tree, with a well-maintained lawn and shrubs lining the front. The entrance features a porch with a welcoming door and matching window shutters, all under a sloped metal roof.

Home in Midway

Country Cottage in Horse and Bourbon Country

This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!

4.89 out of 5 average rating, 9 reviews

Bourbon Central! Prime Location and Amenities

Welcome to your ideal mid-term home in Kentucky. Located 3 minutes from downtown Versailles, this spacious 4-bedroom, 2.5-bath residence is perfect for traveling professionals and corporate stays. Situated in Bourbon Country, it's a short drive to Lexington, Frankfort, Georgetown, and Lawrenceburg. Close to major employers, hospitals, and distilleries, this home offers both convenience and comfort. Relax in expansive living spaces and enjoy all the comforts of home during your extended stay.

4.99 out of 5 average rating, 82 reviews

A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.

Home in Midway

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

A restored Victorian home with intricate architectural details is showcased. A round turret features prominently beside the entrance, which is framed by a welcoming porch and manicured gardens. A wrought-iron fence surrounds the pathway leading to the front door.

5 out of 5 average rating, 15 reviews

Bourbon Trail Beauty

Enjoy this 2023 Fully Restored Gus Macey Victorian in downtown Versailles. Only one block walk to historical Versailles and conveniently located on the Bourbon Trail. 15 mins from Keeneland Racetrack; 20 mins from downtown Lexington. Comfortable for groups of up to 8 with easy access to Woodford Reserve, Castle&Key and Buffalo Trace distilleries. Or tour the world famous Horse Farms, including Coolmore Farm, only minutes away. Have your own Old Kentucky Home in the heart of Kentucky.

4.92 out of 5 average rating, 66 reviews

Home in Frankfort

Whiskey Woods: Newly Remodeled w/ HOT TUB!

Discover Whiskey Woods in picturesque Frankfort, KY! This 3-bed, 2-bath retreat on 3.6 acres offers modern amenities. Enjoy open-concept living, a fully equipped kitchen, and outdoor dining. Explore the lush property with grill. Sleep in plush beds, including a king-sized Whiskey Suite. Stay connected with Wi-Fi, laundry, and parking. Only 1.4 miles from Castle and Key Distillery, and 4.9 miles from Woodford Reserve. Minutes from downtown attractions. Book your Frankfort getaway today!

4.93 out of 5 average rating, 248 reviews

A modern structure with a gray metal roof is positioned on a grassy area, surrounded by gentle rolling hills. A wooden fence borders the property, leading to an illusion of a calm river and a colorful sunrise in the background, creating a serene countryside scene.

Home in Harrodsburg

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

A charming, two-story house is nestled between two large trees, with a wide lawn surrounding it. The home features a porch area and is partially shaded, while warm sunlight casts a long shadow across the grassy yard. A serene, rural setting is highlighted by a wooden fence in the background.

4.95 out of 5 average rating, 176 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

A spacious guest house is set against a clear blue sky, featuring a wraparound porch with white railings. The exterior showcases a combination of light siding and wooden accents, with dormer windows adding charm. Lush green grass surrounds the property.

5 out of 5 average rating, 15 reviews

Home in Versailles on the Bourbon Trail

Guest house on beautiful 172-acre Country Estate in Versailles, KY (Woodford County). Large 4bd/3bth home located directly on Kentucky's famed Bourbon Trail and 15 minutes from the historic Keeneland Racetrack and Bluegrass (Lexington) airport. Bourbon fans will enjoy proximity to famous distilleries such as Woodford Reserve, Four Roses, Buffalo Trace, and more. Visit the locally famous Kentucky Castle and enjoy all the activities of the world renown Kentucky Horse Park and museum.

Superhost

A cozy living area features two large sofas, complementing a rustic wooden coffee table. The space is illuminated by a floor lamp next to one sofa. Artwork, including butterfly prints and nature scenes, decorates the walls, while a patterned area rug adds texture.