House vacation rentals in Woodford County

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Top-rated house rentals in Woodford County

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Top guest favorite

A serene view of the property’s lush green lawn is framed by tall trees, with a faint sunset visible in the distance. A wooden sign displaying 'Birdsong Valley' hangs from a post, surrounded by vibrant foliage. A gently flowing creek is evident, bordered by budding plants.

Home in Versailles

5 out of 5 average rating, 89 reviews

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

Superhost

The exterior of the historic home features a charming blue facade with white trim, complemented by a well-maintained front yard. A wooden fence encloses the garden area, which includes various plants and a decorative bench, creating an inviting entrance. Tree branches and a driveway are also visible.

Home in Versailles

5 out of 5 average rating, 4 reviews

Bourbon Trail & Keeneland Charm

Charming 1903 Historic Home in Versailles, KY Step into history with this beautifully preserved 1903 home, blending vintage charm with modern comfort. Enjoy original hardwood floors, high ceilings, and cozy living spaces. Relax on the charming front porch or explore nearby bourbon distilleries, horse farms, and Keeneland. Just 15 minutes to Lexington, this home is perfect for a peaceful getaway. Book now for a true Kentucky experience! Minutes from Keeneland, Woodford Reserve & Buffalo Trace!

Guest favorite

The image captures a serene view along the Kentucky River. Tree branches frame the scene, with some trees showing signs of early spring. The calm, green water reflects the surrounding landscape, creating a peaceful natural environment.

Home in Kentucky

4.9 out of 5 average rating, 111 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 126 reviews

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!

Guest favorite

A spacious bed is dressed in white linens, adorned with a decorative pillow featuring a horse illustration. Green and tan accent pillows enhance the bed's comfort, while a simple plant adds a touch of greenery. A framed artwork is mounted above the headboard.

Home in Versailles

4.79 out of 5 average rating, 14 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.

Top guest favorite

An open-concept living area features comfortable seating arranged around a circular rug. A well-equipped kitchen is visible in the background, complemented by a dining table for four. Natural light enters through multiple windows, creating a bright and welcoming atmosphere.

Home in Versailles

4.97 out of 5 average rating, 37 reviews

Willow Springs 2br/1ba- Sleeps 8 33 acres w/trails

Built in 2023, this barndominium sits at the end of a private drive surrounded by woods and horse farms. 2 bedrooms (queen and full w/twin trundle), a queen pull-out sofa and full futon comfortably sleep 8. Located only 4 miles from Bluegrass Parkway, there is quick access to local dining, the Bourbon Trail and Rail Explorers. Amenities include Wi-Fi, a laundry room, full kitchen / dining area, patio with grill, and a nature trail through the forest. The reviews tell it better than I do!

Top guest favorite

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

4.93 out of 5 average rating, 251 reviews

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

Top guest favorite

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.

Home in Versailles

4.95 out of 5 average rating, 186 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

Top guest favorite

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.

Home in Versailles

5 out of 5 average rating, 20 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 single-story home is framed by two large trees, featuring a clean, white exterior with wooden shutters. Neatly landscaped gardens line the pathway leading to the entrance, with a black mulch border and strategically placed shrubs, creating a welcoming façade.

Home in Versailles

5 out of 5 average rating, 4 reviews

Bluegrass Bourbon Retreat

Welcome to our cozy & conveniently located retreat! Situated just off Versailles Road, you'll enjoy quick access to Bluegrass Airport, Lexington, & Frankfort, making travel a breeze. We're only minutes away from the iconic Keeneland Racetrack and The Kentucky Castle, perfect for sightseeing and memorable experiences. Start your Bourbon Trail adventure with Woodford Reserve, just 15 mins away. Want to catch a game at Rupp Arena or shop at Fayette Mall both are less than 30mins away.

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.

Home in Versailles

4.84 out of 5 average rating, 89 reviews

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

Top guest favorite

A spacious bedroom features a comfortable king bed adorned with crisp white linens and a cozy grey throw blanket. Two bedside lamps illuminate the room, with a large piece of artwork displayed above the headboard and a plant positioned in the corner.

Home in Wilmore

5 out of 5 average rating, 68 reviews

*KY Charm*Asbury-Lex-Keeneland-King bed-spacious

This spacious, private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and restaurants. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248