House holiday rentals in Woodford County

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.

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!

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!

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

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.

Private Pool 1901 Cottage, Keeneland Bourbon Trail

Minutes from Keeneland racetrack and in the heart of the Bourbon Trail our 1901 cottage has a fenced backyard, patio, grill, private pool open seasonally April to October (unheated) kitchen, laundry, dining room, living room, tv in lr, tv in bedroom and WIFI. A short walk to Main Street restaurants and shops. Minutes from Keeneland Race Track, the Kentucky Horse Park and our world famous Bourbon distilleries, it is surrounded by the most beautiful horse farms in the Bluegrass.

*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

NEW Fireplace, Sunroom, Garden, Bourbon, Downtown

Step into a horse lover’s paradise in Downtown Versailles! Nestled on a Triple Crown-winning horse farm, this retreat offers a front-row seat to equine life all around you. Explore the Bourbon Trail, stopping at Four Roses and Woodford distilleries, & enjoy the season’s charm. With modern amenities and a peaceful countryside setting surrounded by active fields, it’s perfect for families or groups. Your gateway to a memorable Kentucky experience awaits—book now!

Bourbon Trail ~ Pickleball ~ Hot Tub ~ 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. ✔ 3 Comfortable Bedrooms ✔ Bright Living Area ✔ Full Kitchen ✔ 9-hole Duck Duct Putt-Putt Golf Course ✔ DIY Pickleball Court ✔ Vintage Jukebox ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking See more below!